1976 - 1977
ANNUAL REPORT

RESOURCE-RELATED RESEARCH
COMPUTERS AND CHEMISTRY

Grant No. RR-00612

BIOTECHNOLOGY RESOURCES PROGRAM
OF THE
NATIONAL INSTITUTES OF HEALTH

February, 1977

COMPUTER SCIENCE DEPARTMENT
STANFORD UNIVERSITY
Form Approved

 

 

 

 

 

 

 

 

 

 

 

SECTION | OMB No, 68- -R0249
ce mein oop ee co eT sega | GRANT NUMBER (Insert on all pages)
DEPARTMENT OF
HEALTH, EDUCATION, ANO WELFARE SSS 5 R24 RR-00612
PUBLIC HEALTH SERVICE eee .
TOTAL PROIEGT PERIOD
APPLICATION | From 5/1/74 . —_roreugn: 4730077 oe
FOR CONTINUATION GRANT REQUESTED BUDGET PERIOD
{from 8/1/76 __Twrourn: 4/30/77 _
LTTE oe ~
Resource-Related Research Computers and Chemistry ; _
JA. PRINCIPAL INVESTIGATOR OR PROGRAM DIRECTOR & APPLICANT ORGANIZATION (Name and Address-Street, City, State, Zip Code!
(Name and Address, Street, City, State, Zip Code)
DJERASSI, CARL
STANFORD UNIVERSITY STANFORD UNIVERSITY
DEPT. OF CHEMISTRY
STANFORD, CALIF. 94305
28 DtGREEt—™” , ‘Toe soctat Secunity NO.|~=—S*~*S*S*«~CS*SSéR HS ACCOUNT NUMBER oe
PH.D. 1944156365A1
2D. DEPARTMENT, SERVICE, LABORATORY OR EO ~~ "TS" Tie AND ADDRESS OF OFFICIAL IN BUSINESS OFFICE OF APPLICANT
ORGANIZATION
_ CHEMISTRY
7E. MAIQR SUBDIVISION ~~ DEPUTY V. P. FOR BUSINESS & FINANCE
SCH. OF HUMANITI ES AND_ sc I ENCES STANFORD UNIVERSITY
J ORGANIZATIONAL COMPONENT YO RECEIVE CREDIT FOR INSTITUTIONAL STANFORD, CALIF. 94305
GRANT PURPOSES
20 OTHER
7. RESEARCH INVOLVING HUMAN SUBJECTS (See Instructions) "Tg INVENTIONS (See Instructions ww
~ os X Kno {) Ves-not previously reported
Rio UT] Yes APPROVED a Le
Bate Tr. Yea previously reparled
9. PERFORMANCE SITE(S) ee mt eT ene INFORMATION
STANEORD UNIVERSITY Y isa PRINCIPAL INVESTIGATOR | ates Tele Nob Eat
code
DEPARTMENT OF CHEMISTRY or —~
COMPUTER SCIENCE DEPARTMENT PROGRAM DIRECTOR «tem 201 his | 497-2783
DEPARTMTNE OF GENETICS -_ - - {
STANFORD, CALI F. 94305 L1@) Name of dusiness officiel (item 6)
K. D. Creighton bis [497-2251
r iC Name and Uitte ‘of ) agminsatealive - ~ oT
JO. DIREGT COSTS REQUESTED FOR BUDGET PERIOD. ti (iti‘:;™~S™S D'A ne "Oe ” 8
nn owney 415 {497-2 883
$129,931.00 _ Sponsored Projects Dir.
128. CONGRESSIONAL DISTRICT OF APPLICANT ORGANIZATION SHOWN IN ITEM 4 128 COUNTY OF APPLICANT ORGANIZATION SHOWN IN ITEM
TWELFTH SANTA CLARA

 

13 00 NOT USE THIS SPACE

14, CERTIFICATION AND ACCEPYANCE. We, the undersigned, certify thal fhe stptements Nerern are true and cumpiele to Ihe best of Gur &nowledge and
accept, as to any grant awarded, the obligation to comply wih Pubhc Heaith Service terms aan comitions on etfect at tne tme of the awa

154 Caio OGRAM DIRECTUR DATE

 

15. SIGNATURES

{Signatures requiced on orginal =
copy onty Use ina “Per sig | 1oH OFFICIAL SIGNING FOR APPLICAN) ORGANIZATION parl

 

natures mot acceptable )

I H-2540-1 (Formerly Ue 2000-1 ) Wee aeererdbed ty NEE fecual alot, S506 and Lone,
(Rev. 4. 75)
SECTION II—BUDGET

PERSONNEL

NAME (Last, First, “Wnitialy, -
(a)

SECTION It
FROM
May ,

(USUALLY 12 MONTHS)

 

 

A. HEMIZE DIRECT costs REQUESTED | FOR NE NEXT | BUDGET PERIOD

 

TITLE OF POSITION

PRINCIPAL INVESTIGATOR

 

A377

Paprl

April,

[SALARY
REQUESTED

> 1978}

| FRINGE BENEFITS

 

[GRANT NUMBER
RR-00612

(See tnstructions)

 

 

posal ‘for ‘Continued Research
| Submitted May, 1976 —

ape eee ee

 

 

 

 

 

{ ndicate cost of each Item listed

below)

- Subtotals:

 

CONS JLTANT COSTS (See Instructions)

 

 

TOTAL (Columns (6) and (e)

 

EQUIPMENT

 

SUPPLIES

 

 

 

 

DOMESTIC
TRAVEL

 

FOREIGN

 

 

PATIENT COSTS (See instructions)

 

ALTERATIONS AND RENOVATIONS

 

OTHER EXPENSES (ltemize)

TOTAL DIRECY COST (Enter

INDIRECT
cosT

(See Instructions)

 

on Page 1,

Item 10

 

PHS=2540—1 (Former ty “iuezu0e-1)

(Rev. 4+ 75)

)

% S&w*
% TOC’

 

 

Bate af DHEW Agreement:

"PAGE 2

vi this is a spec iat rate (e.g. Off-site}, explain. : an

 
  

YY

I
iy

 

T) Not Requested

* Under negottation with
SECTION 11 (Contiaued)

 

Grant Number

SECTION Il—BUDGET (Continued)
RR~00612

 

 

B. Supplementa! intormation regarding ITEMS in the proposed budget for the next period which require explanation or justification. (See instructions)

See Proposal for Continued Research
1977-80

submitted May, 1976

 

PAGE 3
Poe 2 Gel CRormecty ite 200e—1 }
(Kev. 4~75)
SECTION ti!

 

 

 

SECTION III_FISCAL DATA FOR FROM THROUGH GRANT NUMBER
CURRENT BUDGET PERIOD
(USUALLY 12 MONTHS) 8/1/76 4/30/77 RR-90612

 

The following pertains to your CURRENT PHS budget. Do not include cost sharing funds. This information in conjunction with that provided on Page 2
will be used in determining the amount of support for the NEXT budget period.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

ACTUAL ESTIMATED
CURRENT EXPENDITURES | EXPENDITURES AND | “EXPENDITURES. | UNOLIGATED
BUDGET
A. BUDGET CATEGORIES (As approved by V 31/77 OPREMAINDER ORT MSO z plus | (Subtract Col. 4
awarding unit) (Insert Date) BUOGeT PERIOD Col. 3) fram Col. 1)
qd) (2) (3) (4) (5)
Personnel (Salaries) 100,761 59,784 36 593 96 ,377 4,384
Fringe Benefits 18,943 11,1744 6,953 18,097 846
Consultant Costs - - - - -
Equipment - - - - -
Supplies - 50 10 60 (60)
Domestic 1,400 1,509 1,741 3,250 (1,850)
TRAVEL
Foreign
Patient Costs
Aiterations and Renovations
&
Other 8,827 7,355 4,585 11,940 (3,113)
Total Direct Costs 129,931 79, 842 4g , 882 129,724 207
Indirect Costs (If inctuded in award)
TOTALS ———_——-> | $129 931 + 79,842 $ 49,882 129,724 * 207

 

 

 

 

 

 

Use space below to:
B. List ait items of equipment purchased or expected to be purchased during this budget period which have a unit cost of $1000 or more.

C. Explain any significant batance or deficit shown in any category of Column 5.
D. List all other research support for Principal! Investigator by source, project title, and annual amount.

B. Equipment Purchased

 

 

 

Terminal Rental 3,587 3,957 1,800

Telephone 2,100 2,340 1,080

Publications and

Technical services 2,900 984 1,600
Postage 240 74 105 11,940 (3,113)
D. Research Support for Principal Investigator

NIH AMO4257 Mass Spectrometry in Organic $ 67,700
Biochemistry

NtH GMO6840 Marine chemistry with special 101,490
Emphasis on Steroids

NIH GM20276 Applications of Magnetic ho ,834
Circular Dichrosim

(him25 9001 (F ormer iy Hlie20¢u-" ; BG: 4 ruse Continuation Pages as ve essary

(kev. 4-75)

ee ote
SECTION IV

 

 

 

 

 

APPLICANT. REPEAT GRANT NUMBER SHOWN ON PAGE 1) ————>> GRANT NUMBER
SECTION IV—SUMMARY PROGRESS REPORT RR-00612
PRINCIPAL INVESTIGATOR OR PROGRAM DIRECTOR (Last, First, Initial) PERIOD COVERED BY THIS REPORT
FROM THROUGH
NAME OF ORGANIZATION 8/1/76 4/30/77

 

 

 

TITLE (Repeat title shown in item 1 on first page)

 

1. List publications: (a) published and not previously reported; (b) in press. Provide five reprints if not previously submitted.
2. List ail additions and deletions in professional personne! and any changes in etfort.

3. Progress Report. (See Instructions)

Progress Report Follows

 

Phoe2 9081 (Farmer ty Tibtte2due-1)
(Rev. 4-7,3

PAGE 5

(Use Continuation Page as neasssary)
Resource Related Research - Computers & Chemistry

Stanford University
NIH/BRP Grant RR-00612

Carl Djerassi, Principal Investigator
(Social Security No. )

Research Highlights (1976-77)

1. One of the DENDRAL programs, named CONGEN, continued to
be used by working scientists on problems of biomedical
importance. CONGEN is a complex symbol-manipulation program that
helps working scientists develop hypotheses about the molecular
structure of organic chemical compounds. The scientist provides
structural inferences, the program provides’ the result of
combining the scientist’s partial hypotheses in all plausible
ways. Several scientists across the nation have used the CONGEN
program to help them elucidate molecular structures of naturally-
occurring compounds, We anticipate continued use of this
program, and similar ones, as scientists realize how helpful they
can be for structure elucidation,

2. The Meta-DENDRAL program successfully formulated rules
of mass spectrometry that were new to the sciences These rules,
along with a discussion of the methodology, were published in the

scientific literature [Jnl Am Chem Soc, 98:6168 (1976)]. The
program was tested to see if it could rediscover the rules of
mass spectrometry for two classes of chemical compounds that were
already well understood (amines and estrogenic steroids). Then
it was applied to three classes of compounds whose behavior in a
mass spectrometer was not as well known (mono-, di-, and tri-
ketoandrostanes). The program produced three sets of rules that
explained much of the significant data for these classes. The
time for manual rule formation for these data was estimated to be

several months.
RR-00612 Annual Report

Table of Contents

Section Page
Subsection
1h OVERVIEW OF RESEARCH ACTIVITIES « . «6 « «© © «© « 1
2. EXPERIMENT PLANNER a 5
3. Applications of REACT to Structure Elucidation
Problems a 9
KY CONGEN Developments ye eee we SS
41 Intelligent use of constraining
substructural information . . . « « «© « 15

4,2 New tools for post-pruning CONGEN
structures. os oe ee Uwe YD
5. USE OF CONGEN BY OTHER SCIENTISTS «~« . « « « «© «© 24
5.1 Chemists Using Exported Programs . .« « +» +» 24
5<2 Remote Users of SUMEX. . « «© «© +» «© «© « 26
5.3 Chemists Communicating by Mail . .« « « « « 26

5.4 Chemical Problems Posed to CONGEN. . . +« . 26

6. Stereochemistry in CONGEN « . . «© « «© «© » «© « 30
6. 1 Algori thm ‘ * * * . ° s a . . * 30
6.2 Programming Progress « ~» .« «© « «# « «6 « 31
Ts The GC/HRMS DATA SYSTEM ye eee 8
7.1 Improvements to the Data System * 6 «© wv ws 32
RR-00612 Annual Report

Tv Changes in the Operating System *

7<3 New Developments oe ee
8. META DENDRAL oo. * 4
9. C13 NMR SPECTROMETRY
10. BUDGET er
11. RECENT PUBLICATIONS OF THE HEURISTIC PROGRAMMING
PROJECT a oe we Re

ii