NPASS Compound

Structure

NPC476003 OpenBabel07101718222D 27 27 0 0 1 0 0 0 0 0999 V2000 -11.2583 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -9.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 17 1 0 0 0 0 3 4 1 0 0 0 0 3 5 3 0 0 0 0 4 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 3 0 0 0 0 8 10 2 0 0 0 0 9 11 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 22 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.19
Volume:	412.473
LogP:	4.697
LogD:	3.932
LogS:	-4.758
# Rotatable Bonds:	10
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.305
Synthetic Accessibility Score:	3.518
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.031
MDCK Permeability:	1.7044922060449608e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.807
20% Bioavailability (F20%):	0.742
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	101.04657745361328%
Volume Distribution (VD):	0.644
Pgp-substrate:	1.1515369415283203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.879
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.267
CYP2C9-inhibitor:	0.95
CYP2C9-substrate:	0.997
CYP2D6-inhibitor:	0.915
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	6.224
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.534
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.957
Carcinogencity:	0.568
Eye Corrosion:	0.025
Eye Irritation:	0.968
Respiratory Toxicity:	0.248

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC476003

Natural Product ID:	NPC476003
*Common Name:**	14-Hydroxyheptadeca-8,10,12-Trien-4,6-Diynyl Benzoate
IUPAC Name:	[(8E,10E,12E)-14-hydroxyheptadeca-8,10,12-trien-4,6-diynyl] benzoate
Synonyms:
Standard InCHIKey:	XGDWMJXBOWGAFH-RVHBMOCVSA-N
Standard InCHI:	InChI=1S/C24H26O3/c1-2-17-23(25)20-15-10-8-6-4-3-5-7-9-11-16-21-27-24(26)22-18-13-12-14-19-22/h4,6,8,10,12-15,18-20,23,25H,2,11,16-17,21H2,1H3/b6-4+,10-8+,20-15+
SMILES:	CCCC(/C=C/C=C/C=C/C#CC#CCCCOC(=O)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521069
PubChem CID:	44559589
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO18052	Cicuta maculata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572419]
NPO18052	Cicuta maculata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[571517]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC476003 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	954
0.2-0.3	2989
0.3-0.4	8328
0.4-0.5	11314
0.5-0.6	12567
0.6-0.7	5618
0.7-0.8	625
0.8-0.85	64
0.85-0.9	33
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8942	High Similarity	NPC474365
0.8942	High Similarity	NPC301943
0.8922	High Similarity	NPC78701
0.8922	High Similarity	NPC35448
0.8909	High Similarity	NPC474685
0.8835	High Similarity	NPC325497
0.8835	High Similarity	NPC146351
0.8824	High Similarity	NPC276775
0.8824	High Similarity	NPC92754
0.8824	High Similarity	NPC249912
0.8818	High Similarity	NPC474363
0.8807	High Similarity	NPC158282
0.8738	High Similarity	NPC225060
0.8727	High Similarity	NPC272524
0.8704	High Similarity	NPC469636
0.8649	High Similarity	NPC153053
0.8636	High Similarity	NPC321852
0.8636	High Similarity	NPC474314
0.8627	High Similarity	NPC130398
0.8571	High Similarity	NPC210092
0.8571	High Similarity	NPC70624
0.8545	High Similarity	NPC260818
0.8532	High Similarity	NPC474364
0.8476	Intermediate Similarity	NPC118343
0.8426	Intermediate Similarity	NPC269457
0.8396	Intermediate Similarity	NPC42211
0.8393	Intermediate Similarity	NPC128368
0.8378	Intermediate Similarity	NPC474157
0.8364	Intermediate Similarity	NPC83628
0.8364	Intermediate Similarity	NPC269023
0.8364	Intermediate Similarity	NPC99846
0.8364	Intermediate Similarity	NPC85493
0.8364	Intermediate Similarity	NPC17417
0.8364	Intermediate Similarity	NPC10251
0.8364	Intermediate Similarity	NPC265407
0.8319	Intermediate Similarity	NPC307651
0.8318	Intermediate Similarity	NPC188895
0.8302	Intermediate Similarity	NPC203925
0.8288	Intermediate Similarity	NPC93084
0.8288	Intermediate Similarity	NPC214067
0.8288	Intermediate Similarity	NPC251854
0.8288	Intermediate Similarity	NPC196246
0.8286	Intermediate Similarity	NPC253423
0.8273	Intermediate Similarity	NPC56493
0.8246	Intermediate Similarity	NPC306740
0.8241	Intermediate Similarity	NPC160382
0.8235	Intermediate Similarity	NPC62765
0.823	Intermediate Similarity	NPC161611
0.8214	Intermediate Similarity	NPC305912
0.8214	Intermediate Similarity	NPC1082
0.8208	Intermediate Similarity	NPC229242
0.8205	Intermediate Similarity	NPC90522
0.8205	Intermediate Similarity	NPC328459
0.8182	Intermediate Similarity	NPC119271
0.8182	Intermediate Similarity	NPC275576
0.8174	Intermediate Similarity	NPC100353
0.8158	Intermediate Similarity	NPC237366
0.8148	Intermediate Similarity	NPC25458
0.8142	Intermediate Similarity	NPC82899
0.8142	Intermediate Similarity	NPC270699
0.8137	Intermediate Similarity	NPC173443
0.8136	Intermediate Similarity	NPC72977
0.8131	Intermediate Similarity	NPC217621
0.8125	Intermediate Similarity	NPC174099
0.812	Intermediate Similarity	NPC94637
0.812	Intermediate Similarity	NPC27633
0.812	Intermediate Similarity	NPC94298
0.8115	Intermediate Similarity	NPC110211
0.8115	Intermediate Similarity	NPC169913
0.8091	Intermediate Similarity	NPC209632
0.8087	Intermediate Similarity	NPC81808
0.8083	Intermediate Similarity	NPC223351
0.8073	Intermediate Similarity	NPC89886
0.8053	Intermediate Similarity	NPC210089
0.8037	Intermediate Similarity	NPC175852
0.8037	Intermediate Similarity	NPC210529
0.8037	Intermediate Similarity	NPC160548
0.8033	Intermediate Similarity	NPC49938
0.8019	Intermediate Similarity	NPC61944
0.8018	Intermediate Similarity	NPC30594
0.8018	Intermediate Similarity	NPC472315
0.8018	Intermediate Similarity	NPC474376
0.8018	Intermediate Similarity	NPC136962
0.8018	Intermediate Similarity	NPC475203
0.8018	Intermediate Similarity	NPC37622
0.8018	Intermediate Similarity	NPC472316
0.8017	Intermediate Similarity	NPC471466
0.8	Intermediate Similarity	NPC308744
0.8	Intermediate Similarity	NPC114594
0.8	Intermediate Similarity	NPC31786
0.8	Intermediate Similarity	NPC249067
0.7982	Intermediate Similarity	NPC304873
0.7967	Intermediate Similarity	NPC472706
0.7967	Intermediate Similarity	NPC204579
0.7961	Intermediate Similarity	NPC220893
0.7951	Intermediate Similarity	NPC246166
0.7951	Intermediate Similarity	NPC221798
0.7949	Intermediate Similarity	NPC131192
0.7949	Intermediate Similarity	NPC128825
0.7946	Intermediate Similarity	NPC20485
0.7944	Intermediate Similarity	NPC289201
0.7941	Intermediate Similarity	NPC89377
0.7934	Intermediate Similarity	NPC472703
0.7913	Intermediate Similarity	NPC474176
0.7909	Intermediate Similarity	NPC60679
0.7909	Intermediate Similarity	NPC91820
0.7909	Intermediate Similarity	NPC82426
0.7903	Intermediate Similarity	NPC472707
0.7881	Intermediate Similarity	NPC469574
0.7881	Intermediate Similarity	NPC240664
0.7869	Intermediate Similarity	NPC472704
0.7869	Intermediate Similarity	NPC228739
0.7864	Intermediate Similarity	NPC304760
0.7863	Intermediate Similarity	NPC149691
0.7845	Intermediate Similarity	NPC87069
0.7843	Intermediate Similarity	NPC318107
0.7838	Intermediate Similarity	NPC280616
0.7838	Intermediate Similarity	NPC171831
0.7838	Intermediate Similarity	NPC242913
0.7833	Intermediate Similarity	NPC473243
0.7833	Intermediate Similarity	NPC233282
0.7823	Intermediate Similarity	NPC473220
0.7823	Intermediate Similarity	NPC114096
0.7823	Intermediate Similarity	NPC470753
0.7818	Intermediate Similarity	NPC284477
0.7818	Intermediate Similarity	NPC45613
0.781	Intermediate Similarity	NPC119631
0.7805	Intermediate Similarity	NPC184219
0.7805	Intermediate Similarity	NPC295664
0.7798	Intermediate Similarity	NPC228435
0.7795	Intermediate Similarity	NPC233692
0.7795	Intermediate Similarity	NPC104854
0.7788	Intermediate Similarity	NPC211439
0.7788	Intermediate Similarity	NPC249811
0.7787	Intermediate Similarity	NPC291189
0.7787	Intermediate Similarity	NPC69403
0.7778	Intermediate Similarity	NPC270654
0.7769	Intermediate Similarity	NPC50872
0.7768	Intermediate Similarity	NPC472919
0.7768	Intermediate Similarity	NPC105899
0.776	Intermediate Similarity	NPC148026
0.7759	Intermediate Similarity	NPC265002
0.775	Intermediate Similarity	NPC204784
0.775	Intermediate Similarity	NPC472708
0.775	Intermediate Similarity	NPC61779
0.7748	Intermediate Similarity	NPC255676
0.7745	Intermediate Similarity	NPC58616
0.7742	Intermediate Similarity	NPC470765
0.7739	Intermediate Similarity	NPC243355
0.7739	Intermediate Similarity	NPC167504
0.7736	Intermediate Similarity	NPC77273
0.7727	Intermediate Similarity	NPC282895
0.7719	Intermediate Similarity	NPC31274
0.7719	Intermediate Similarity	NPC281604
0.7717	Intermediate Similarity	NPC72915
0.7699	Intermediate Similarity	NPC477251
0.7699	Intermediate Similarity	NPC37115
0.7698	Intermediate Similarity	NPC473744
0.7698	Intermediate Similarity	NPC2596
0.7698	Intermediate Similarity	NPC301857
0.7674	Intermediate Similarity	NPC311492
0.7674	Intermediate Similarity	NPC38420
0.7674	Intermediate Similarity	NPC136608
0.7674	Intermediate Similarity	NPC28836
0.7672	Intermediate Similarity	NPC234376
0.7672	Intermediate Similarity	NPC79496
0.7664	Intermediate Similarity	NPC261181
0.7656	Intermediate Similarity	NPC239358
0.7647	Intermediate Similarity	NPC128249
0.7642	Intermediate Similarity	NPC110704
0.7642	Intermediate Similarity	NPC67300
0.7638	Intermediate Similarity	NPC272946
0.7638	Intermediate Similarity	NPC238309
0.7638	Intermediate Similarity	NPC194979
0.7632	Intermediate Similarity	NPC156648
0.7632	Intermediate Similarity	NPC277788
0.7615	Intermediate Similarity	NPC477896
0.7615	Intermediate Similarity	NPC232888
0.7615	Intermediate Similarity	NPC477893
0.7615	Intermediate Similarity	NPC477367
0.7615	Intermediate Similarity	NPC474097
0.7607	Intermediate Similarity	NPC17693
0.76	Intermediate Similarity	NPC4164
0.7597	Intermediate Similarity	NPC477364
0.7597	Intermediate Similarity	NPC472248
0.7597	Intermediate Similarity	NPC302844
0.7589	Intermediate Similarity	NPC304638
0.7583	Intermediate Similarity	NPC45104
0.7583	Intermediate Similarity	NPC217423
0.7573	Intermediate Similarity	NPC294134
0.7568	Intermediate Similarity	NPC469481
0.7565	Intermediate Similarity	NPC206341
0.7565	Intermediate Similarity	NPC469511
0.7563	Intermediate Similarity	NPC471616
0.7561	Intermediate Similarity	NPC26285
0.7557	Intermediate Similarity	NPC472374
0.7557	Intermediate Similarity	NPC472372
0.7557	Intermediate Similarity	NPC52523
0.7557	Intermediate Similarity	NPC202729
0.7557	Intermediate Similarity	NPC217673

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC476003 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	744
0.2-0.3	1461
0.3-0.4	2697
0.4-0.5	2380
0.5-0.6	1244
0.6-0.7	382
0.7-0.8	55
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8545	High Similarity	NPD2181	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD1238	Approved
0.8364	Intermediate Similarity	NPD2182	Approved
0.8235	Intermediate Similarity	NPD9256	Approved
0.8235	Intermediate Similarity	NPD9258	Approved
0.812	Intermediate Similarity	NPD9545	Approved
0.8037	Intermediate Similarity	NPD9495	Approved
0.8	Intermediate Similarity	NPD1237	Approved
0.8	Intermediate Similarity	NPD164	Approved
0.7949	Intermediate Similarity	NPD9493	Approved
0.7909	Intermediate Similarity	NPD6647	Phase 2
0.7876	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD9257	Approved
0.7843	Intermediate Similarity	NPD9259	Approved
0.7778	Intermediate Similarity	NPD2629	Approved
0.7664	Intermediate Similarity	NPD1202	Approved
0.7638	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7008	Discontinued
0.7627	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5277	Phase 2
0.7541	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD5909	Discontinued
0.752	Intermediate Similarity	NPD2199	Approved
0.752	Intermediate Similarity	NPD2198	Approved
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD2067	Discontinued
0.7481	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD5951	Approved
0.7477	Intermediate Similarity	NPD2066	Phase 3
0.7434	Intermediate Similarity	NPD1929	Approved
0.7434	Intermediate Similarity	NPD1930	Approved
0.7434	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6287	Discontinued
0.7398	Intermediate Similarity	NPD5306	Approved
0.7398	Intermediate Similarity	NPD5305	Approved
0.7379	Intermediate Similarity	NPD9491	Approved
0.7328	Intermediate Similarity	NPD9264	Approved
0.7328	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9263	Approved
0.7328	Intermediate Similarity	NPD9267	Approved
0.729	Intermediate Similarity	NPD800	Approved
0.7273	Intermediate Similarity	NPD9260	Approved
0.7265	Intermediate Similarity	NPD9266	Approved
0.7265	Intermediate Similarity	NPD74	Approved
0.7241	Intermediate Similarity	NPD3134	Approved
0.7227	Intermediate Similarity	NPD9508	Approved
0.7227	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD1090	Approved
0.7222	Intermediate Similarity	NPD1089	Approved
0.7222	Intermediate Similarity	NPD1086	Approved
0.7207	Intermediate Similarity	NPD1989	Approved
0.7188	Intermediate Similarity	NPD1203	Approved
0.7182	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5159	Phase 2
0.7165	Intermediate Similarity	NPD5157	Phase 1
0.7155	Intermediate Similarity	NPD5048	Discontinued
0.7154	Intermediate Similarity	NPD6832	Phase 2
0.7132	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6085	Phase 2
0.713	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD689	Discontinued
0.7117	Intermediate Similarity	NPD1693	Approved
0.7107	Intermediate Similarity	NPD1241	Discontinued
0.7103	Intermediate Similarity	NPD1282	Approved
0.7097	Intermediate Similarity	NPD1894	Discontinued
0.7091	Intermediate Similarity	NPD1088	Approved
0.7083	Intermediate Similarity	NPD969	Suspended
0.7073	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD3672	Approved
0.7064	Intermediate Similarity	NPD3673	Approved
0.7063	Intermediate Similarity	NPD4106	Approved
0.7063	Intermediate Similarity	NPD4135	Approved
0.7063	Intermediate Similarity	NPD4136	Approved
0.7054	Intermediate Similarity	NPD2797	Approved
0.7054	Intermediate Similarity	NPD2160	Approved
0.7054	Intermediate Similarity	NPD2627	Approved
0.7054	Intermediate Similarity	NPD2159	Approved
0.7054	Intermediate Similarity	NPD2625	Approved
0.7054	Intermediate Similarity	NPD2628	Approved
0.7054	Intermediate Similarity	NPD2626	Approved
0.7045	Intermediate Similarity	NPD3764	Approved
0.7043	Intermediate Similarity	NPD1932	Approved
0.7034	Intermediate Similarity	NPD1358	Approved
0.7029	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD226	Approved
0.7015	Intermediate Similarity	NPD230	Phase 1
0.7008	Intermediate Similarity	NPD4807	Approved
0.7008	Intermediate Similarity	NPD4806	Approved
0.7007	Intermediate Similarity	NPD6002	Phase 3
0.7007	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6005	Phase 3
0.7007	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1019	Discontinued
0.6992	Remote Similarity	NPD4198	Discontinued
0.699	Remote Similarity	NPD9490	Approved
0.6984	Remote Similarity	NPD1104	Approved
0.6984	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9261	Approved
0.6972	Remote Similarity	NPD5346	Phase 2
0.6972	Remote Similarity	NPD5347	Phase 2
0.697	Remote Similarity	NPD6966	Discovery
0.6967	Remote Similarity	NPD6010	Discontinued
0.6961	Remote Similarity	NPD9294	Approved
0.6944	Remote Similarity	NPD1087	Approved
0.6944	Remote Similarity	NPD4793	Discontinued
0.6934	Remote Similarity	NPD2935	Discontinued
0.6923	Remote Similarity	NPD9567	Approved
0.6923	Remote Similarity	NPD552	Approved
0.6923	Remote Similarity	NPD553	Approved
0.6917	Remote Similarity	NPD2313	Discontinued
0.6917	Remote Similarity	NPD411	Approved
0.6912	Remote Similarity	NPD2567	Approved
0.6912	Remote Similarity	NPD2569	Approved
0.6911	Remote Similarity	NPD9281	Approved
0.6905	Remote Similarity	NPD4102	Approved
0.6905	Remote Similarity	NPD4105	Approved
0.6889	Remote Similarity	NPD447	Suspended
0.6884	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2798	Approved
0.687	Remote Similarity	NPD5647	Approved
0.6861	Remote Similarity	NPD2799	Discontinued
0.6861	Remote Similarity	NPD4308	Phase 3
0.6857	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6273	Approved
0.685	Remote Similarity	NPD1778	Approved
0.6847	Remote Similarity	NPD1239	Approved
0.6846	Remote Similarity	NPD5667	Approved
0.6842	Remote Similarity	NPD6039	Approved
0.6833	Remote Similarity	NPD2329	Discontinued
0.6829	Remote Similarity	NPD2652	Approved
0.6829	Remote Similarity	NPD2650	Approved
0.6828	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3972	Approved
0.6818	Remote Similarity	NPD3661	Approved
0.6818	Remote Similarity	NPD5204	Approved
0.6818	Remote Similarity	NPD9494	Approved
0.6818	Remote Similarity	NPD3664	Approved
0.6818	Remote Similarity	NPD3662	Phase 3
0.6818	Remote Similarity	NPD3663	Approved
0.6815	Remote Similarity	NPD3373	Approved
0.6812	Remote Similarity	NPD1551	Phase 2
0.6807	Remote Similarity	NPD6685	Approved
0.6797	Remote Similarity	NPD3496	Discontinued
0.6791	Remote Similarity	NPD3268	Approved
0.6791	Remote Similarity	NPD6798	Discontinued
0.6783	Remote Similarity	NPD5926	Approved
0.6777	Remote Similarity	NPD1317	Discontinued
0.6767	Remote Similarity	NPD5201	Approved
0.6767	Remote Similarity	NPD4617	Approved
0.6767	Remote Similarity	NPD4620	Approved
0.6767	Remote Similarity	NPD5203	Approved
0.6765	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD9716	Approved
0.6761	Remote Similarity	NPD7440	Discontinued
0.6759	Remote Similarity	NPD7239	Suspended
0.6746	Remote Similarity	NPD2347	Approved
0.6741	Remote Similarity	NPD7713	Phase 3
0.6741	Remote Similarity	NPD4062	Phase 3
0.6741	Remote Similarity	NPD520	Approved
0.6741	Remote Similarity	NPD6233	Phase 2
0.6738	Remote Similarity	NPD7003	Approved
0.6731	Remote Similarity	NPD225	Approved
0.6731	Remote Similarity	NPD227	Approved
0.6724	Remote Similarity	NPD7798	Approved
0.6716	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3455	Phase 2
0.6696	Remote Similarity	NPD1564	Approved
0.6696	Remote Similarity	NPD1566	Phase 3
0.6696	Remote Similarity	NPD1565	Approved
0.6692	Remote Similarity	NPD1481	Phase 2
0.6692	Remote Similarity	NPD1608	Approved
0.669	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD5292	Approved
0.6667	Remote Similarity	NPD5291	Approved
0.6667	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD6362	Approved
0.6667	Remote Similarity	NPD2670	Approved
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2346	Discontinued
0.6642	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6355	Discontinued
0.6642	Remote Similarity	NPD1933	Approved
0.6641	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5585	Approved
0.664	Remote Similarity	NPD1246	Approved
0.6639	Remote Similarity	NPD5235	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data