NPASS Compound

Structure

NPC163902 OpenBabel07101718182D 38 42 0 0 1 0 0 0 0 0999 V2000 4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3685 -1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6994 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 -2.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 21 1 0 0 0 0 14 24 1 0 0 0 0 15 23 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 35 1 0 0 0 0 17 32 2 0 0 0 0 17 36 1 0 0 0 0 18 33 2 0 0 0 0 18 37 1 0 0 0 0 19 34 2 0 0 0 0 19 38 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 36 1 1 0 0 0 22 28 1 0 0 0 0 22 29 1 1 0 0 0 23 29 1 1 0 0 0 23 30 1 0 0 0 0 24 30 1 1 0 0 0 24 31 1 0 0 0 0 25 31 1 1 0 0 0 25 37 1 0 0 0 0 26 27 1 0 0 0 0 26 31 1 1 0 0 0 27 35 1 0 0 0 0 27 38 1 6 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.32
Volume:	552.935
LogP:	4.699
LogD:	3.907
LogS:	-4.586
# Rotatable Bonds:	6
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	5.204
Fsp3:	0.839
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	0.00012556975707411766
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.673
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.483
Plasma Protein Binding (PPB):	81.89771270751953%
Volume Distribution (VD):	2.279
Pgp-substrate:	16.687721252441406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.716
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.584
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.604
CYP3A4-substrate:	0.531

ADMET: Excretion

Clearance (CL):	3.274
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.532
Human Hepatotoxicity (H-HT):	0.721
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.408
Carcinogencity:	0.372
Eye Corrosion:	0.326
Eye Irritation:	0.039
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC163902

Natural Product ID:	NPC163902
*Common Name:**	Heteronemin Acetate
IUPAC Name:	[(1S,4S,5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-1,13-diacetyloxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-4-yl] acetate
Synonyms:	16-O-Acetylheteronemin; Heteronemin Acetate
Standard InCHIKey:	HZGUZCQEPZRJOT-ONZUFQJTSA-N
Standard InCHI:	InChI=1S/C31H46O7/c1-17(32)36-21-14-24-30(7)13-10-22-28(4,5)11-9-12-29(22,6)23(30)15-25(37-18(2)33)31(24,8)26-20(21)16-35-27(26)38-19(3)34/h16,21-27H,9-15H2,1-8H3/t21-,22-,23+,24-,25+,26+,27-,29-,30+,31+/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2[C@@]([C@H]3[C@@]1(C)[C@H]1[C@@H](OC=C1[C@H](C3)OC(=O)C)OC(=O)C)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503225
PubChem CID:	21589811
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33331	brachiaster sp.	Species	n.a.	n.a.	n.a.	Thai	n.a.	PMID[15497961]

☑ 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
IC50	6
MIC	1
Others	3

Activity Type	# Activity
Cell Line	8
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6450.0	nM	PMID[545452]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	80.0	%	PMID[545452]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	80.0	%	PMID[545452]
NPT91	Cell Line	KB	Homo sapiens	Activity	=	80.0	%	PMID[545452]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	18800.0	nM	PMID[545453]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	=	16700.0	nM	PMID[545453]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	18800.0	nM	PMID[545453]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	9000.0	nM	PMID[545453]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	6000.0	nM	PMID[545452]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	18800.0	nM	PMID[545453]

☑ 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 NPC163902 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	283
0.1-0.2	2325
0.2-0.3	5988
0.3-0.4	14342
0.4-0.5	9233
0.5-0.6	5727
0.6-0.7	3867
0.7-0.8	909
0.8-0.85	15
0.85-0.9	4
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC97867
0.9535	High Similarity	NPC144069
0.9111	High Similarity	NPC246860
0.8817	High Similarity	NPC8954
0.8817	High Similarity	NPC164750
0.8817	High Similarity	NPC94905
0.8791	High Similarity	NPC120539
0.8351	Intermediate Similarity	NPC20113
0.8351	Intermediate Similarity	NPC477971
0.8351	Intermediate Similarity	NPC228251
0.8351	Intermediate Similarity	NPC477968
0.8351	Intermediate Similarity	NPC161527
0.8351	Intermediate Similarity	NPC219285
0.8351	Intermediate Similarity	NPC477972
0.8298	Intermediate Similarity	NPC12297
0.8242	Intermediate Similarity	NPC471369
0.8222	Intermediate Similarity	NPC471367
0.8211	Intermediate Similarity	NPC477722
0.8125	Intermediate Similarity	NPC472189
0.8125	Intermediate Similarity	NPC471362
0.8125	Intermediate Similarity	NPC471372
0.8111	Intermediate Similarity	NPC473742
0.8043	Intermediate Similarity	NPC471368
0.8041	Intermediate Similarity	NPC171598
0.7979	Intermediate Similarity	NPC293044
0.7978	Intermediate Similarity	NPC475456
0.7959	Intermediate Similarity	NPC113976
0.7959	Intermediate Similarity	NPC472188
0.7959	Intermediate Similarity	NPC198549
0.7957	Intermediate Similarity	NPC288952
0.7938	Intermediate Similarity	NPC100892
0.7938	Intermediate Similarity	NPC135224
0.7938	Intermediate Similarity	NPC477969
0.7938	Intermediate Similarity	NPC477970
0.7921	Intermediate Similarity	NPC120009
0.7885	Intermediate Similarity	NPC112457
0.7879	Intermediate Similarity	NPC471366
0.7879	Intermediate Similarity	NPC472186
0.7879	Intermediate Similarity	NPC476800
0.7879	Intermediate Similarity	NPC318917
0.7872	Intermediate Similarity	NPC263079
0.7835	Intermediate Similarity	NPC3359
0.7835	Intermediate Similarity	NPC189513
0.7822	Intermediate Similarity	NPC177701
0.7812	Intermediate Similarity	NPC130840
0.78	Intermediate Similarity	NPC473545
0.78	Intermediate Similarity	NPC477716
0.78	Intermediate Similarity	NPC324841
0.78	Intermediate Similarity	NPC473204
0.78	Intermediate Similarity	NPC146188
0.78	Intermediate Similarity	NPC472187
0.78	Intermediate Similarity	NPC477721
0.7791	Intermediate Similarity	NPC12680
0.7778	Intermediate Similarity	NPC304194
0.7778	Intermediate Similarity	NPC51499
0.7767	Intermediate Similarity	NPC165405
0.7745	Intermediate Similarity	NPC45897
0.7745	Intermediate Similarity	NPC281378
0.7742	Intermediate Similarity	NPC474013
0.7723	Intermediate Similarity	NPC477717
0.7717	Intermediate Similarity	NPC474284
0.7717	Intermediate Similarity	NPC475820
0.7717	Intermediate Similarity	NPC474346
0.7717	Intermediate Similarity	NPC474253
0.7717	Intermediate Similarity	NPC213737
0.7708	Intermediate Similarity	NPC471370
0.7708	Intermediate Similarity	NPC471371
0.77	Intermediate Similarity	NPC325229
0.77	Intermediate Similarity	NPC275086
0.7692	Intermediate Similarity	NPC470170
0.7692	Intermediate Similarity	NPC475074
0.7692	Intermediate Similarity	NPC470169
0.7684	Intermediate Similarity	NPC106332
0.7677	Intermediate Similarity	NPC317573
0.767	Intermediate Similarity	NPC476763
0.767	Intermediate Similarity	NPC222161
0.767	Intermediate Similarity	NPC476764
0.7667	Intermediate Similarity	NPC305835
0.766	Intermediate Similarity	NPC118266
0.7653	Intermediate Similarity	NPC88507
0.7647	Intermediate Similarity	NPC238397
0.7647	Intermediate Similarity	NPC471363
0.764	Intermediate Similarity	NPC84868
0.7634	Intermediate Similarity	NPC299963
0.7629	Intermediate Similarity	NPC329842
0.7624	Intermediate Similarity	NPC317019
0.7619	Intermediate Similarity	NPC325054
0.7609	Intermediate Similarity	NPC208912
0.7609	Intermediate Similarity	NPC472504
0.7609	Intermediate Similarity	NPC2096
0.76	Intermediate Similarity	NPC473555
0.76	Intermediate Similarity	NPC477719
0.76	Intermediate Similarity	NPC278939
0.76	Intermediate Similarity	NPC471770
0.76	Intermediate Similarity	NPC477718
0.7596	Intermediate Similarity	NPC476760
0.7596	Intermediate Similarity	NPC476762
0.7596	Intermediate Similarity	NPC470056
0.7596	Intermediate Similarity	NPC476761
0.7596	Intermediate Similarity	NPC470055
0.7596	Intermediate Similarity	NPC51719
0.7593	Intermediate Similarity	NPC157441
0.7582	Intermediate Similarity	NPC469802
0.7579	Intermediate Similarity	NPC175293
0.7573	Intermediate Similarity	NPC7613
0.7573	Intermediate Similarity	NPC127933
0.7573	Intermediate Similarity	NPC134270
0.7573	Intermediate Similarity	NPC7644
0.7573	Intermediate Similarity	NPC475889
0.7553	Intermediate Similarity	NPC164424
0.7551	Intermediate Similarity	NPC473678
0.7551	Intermediate Similarity	NPC7349
0.7551	Intermediate Similarity	NPC474835
0.7551	Intermediate Similarity	NPC26046
0.7547	Intermediate Similarity	NPC31522
0.7547	Intermediate Similarity	NPC206618
0.7527	Intermediate Similarity	NPC127917
0.7527	Intermediate Similarity	NPC132386
0.7526	Intermediate Similarity	NPC475776
0.7526	Intermediate Similarity	NPC194485
0.7526	Intermediate Similarity	NPC53890
0.7526	Intermediate Similarity	NPC123252
0.7526	Intermediate Similarity	NPC219937
0.7525	Intermediate Similarity	NPC477928
0.7525	Intermediate Similarity	NPC157739
0.7524	Intermediate Similarity	NPC470166
0.7523	Intermediate Similarity	NPC84949
0.7523	Intermediate Similarity	NPC69576
0.7523	Intermediate Similarity	NPC31354
0.7523	Intermediate Similarity	NPC471633
0.75	Intermediate Similarity	NPC264867
0.75	Intermediate Similarity	NPC194951
0.75	Intermediate Similarity	NPC194132
0.75	Intermediate Similarity	NPC12046
0.75	Intermediate Similarity	NPC173583
0.75	Intermediate Similarity	NPC470321
0.75	Intermediate Similarity	NPC81567
0.75	Intermediate Similarity	NPC160304
0.75	Intermediate Similarity	NPC473125
0.75	Intermediate Similarity	NPC473207
0.75	Intermediate Similarity	NPC311166
0.75	Intermediate Similarity	NPC201880
0.7477	Intermediate Similarity	NPC177047
0.7476	Intermediate Similarity	NPC31085
0.7476	Intermediate Similarity	NPC121423
0.7475	Intermediate Similarity	NPC211238
0.7475	Intermediate Similarity	NPC140277
0.7475	Intermediate Similarity	NPC105490
0.7474	Intermediate Similarity	NPC102996
0.7474	Intermediate Similarity	NPC168231
0.7474	Intermediate Similarity	NPC286153
0.7455	Intermediate Similarity	NPC199428
0.7455	Intermediate Similarity	NPC5311
0.7455	Intermediate Similarity	NPC193382
0.7455	Intermediate Similarity	NPC99620
0.7455	Intermediate Similarity	NPC310341
0.7453	Intermediate Similarity	NPC38948
0.7453	Intermediate Similarity	NPC300614
0.7453	Intermediate Similarity	NPC90946
0.7453	Intermediate Similarity	NPC473517
0.7453	Intermediate Similarity	NPC88744
0.7451	Intermediate Similarity	NPC471247
0.7449	Intermediate Similarity	NPC472811
0.7431	Intermediate Similarity	NPC290608
0.7431	Intermediate Similarity	NPC40133
0.7431	Intermediate Similarity	NPC44298
0.7431	Intermediate Similarity	NPC49413
0.7431	Intermediate Similarity	NPC473128
0.7429	Intermediate Similarity	NPC172867
0.7429	Intermediate Similarity	NPC218158
0.7429	Intermediate Similarity	NPC252296
0.7429	Intermediate Similarity	NPC291414
0.7429	Intermediate Similarity	NPC473199
0.7426	Intermediate Similarity	NPC274793
0.7426	Intermediate Similarity	NPC98112
0.7423	Intermediate Similarity	NPC470819
0.7419	Intermediate Similarity	NPC286786
0.7411	Intermediate Similarity	NPC268326
0.7411	Intermediate Similarity	NPC470914
0.7411	Intermediate Similarity	NPC304260
0.7411	Intermediate Similarity	NPC29639
0.7411	Intermediate Similarity	NPC153085
0.7411	Intermediate Similarity	NPC44899
0.7411	Intermediate Similarity	NPC5883
0.7407	Intermediate Similarity	NPC470311
0.7407	Intermediate Similarity	NPC270586
0.7404	Intermediate Similarity	NPC254202
0.7404	Intermediate Similarity	NPC165608
0.7404	Intermediate Similarity	NPC471467
0.7404	Intermediate Similarity	NPC473124
0.7404	Intermediate Similarity	NPC473123
0.7404	Intermediate Similarity	NPC471208
0.74	Intermediate Similarity	NPC276110
0.7396	Intermediate Similarity	NPC102640
0.7387	Intermediate Similarity	NPC93883
0.7387	Intermediate Similarity	NPC158344
0.7387	Intermediate Similarity	NPC290693
0.7387	Intermediate Similarity	NPC244402
0.7387	Intermediate Similarity	NPC471354
0.7387	Intermediate Similarity	NPC243196

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 NPC163902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	2513
0.2-0.3	3853
0.3-0.4	1785
0.4-0.5	472
0.5-0.6	222
0.6-0.7	36
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7321	Intermediate Similarity	NPD7328	Approved
0.7321	Intermediate Similarity	NPD7327	Approved
0.7281	Intermediate Similarity	NPD8033	Approved
0.7273	Intermediate Similarity	NPD8133	Approved
0.7257	Intermediate Similarity	NPD7516	Approved
0.7193	Intermediate Similarity	NPD8377	Approved
0.7193	Intermediate Similarity	NPD8294	Approved
0.7184	Intermediate Similarity	NPD7638	Approved
0.713	Intermediate Similarity	NPD8296	Approved
0.713	Intermediate Similarity	NPD8380	Approved
0.713	Intermediate Similarity	NPD8379	Approved
0.713	Intermediate Similarity	NPD8335	Approved
0.713	Intermediate Similarity	NPD8378	Approved
0.7115	Intermediate Similarity	NPD7639	Approved
0.7115	Intermediate Similarity	NPD7640	Approved
0.71	Intermediate Similarity	NPD8034	Phase 2
0.71	Intermediate Similarity	NPD8035	Phase 2
0.6983	Remote Similarity	NPD7503	Approved
0.6972	Remote Similarity	NPD6686	Approved
0.6891	Remote Similarity	NPD7507	Approved
0.6837	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7900	Approved
0.6721	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6638	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7748	Approved
0.6607	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7902	Approved
0.6569	Remote Similarity	NPD6051	Approved
0.6446	Remote Similarity	NPD8328	Phase 3
0.6442	Remote Similarity	NPD7515	Phase 2
0.6429	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7645	Phase 2
0.6381	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6008	Approved
0.6327	Remote Similarity	NPD7525	Registered
0.6327	Remote Similarity	NPD6928	Phase 2
0.6316	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7736	Approved
0.6239	Remote Similarity	NPD4225	Approved
0.6238	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6697	Approved
0.6122	Remote Similarity	NPD6118	Approved
0.6122	Remote Similarity	NPD6115	Approved
0.6122	Remote Similarity	NPD6114	Approved
0.6117	Remote Similarity	NPD6409	Approved
0.6117	Remote Similarity	NPD7146	Approved
0.6117	Remote Similarity	NPD7334	Approved
0.6117	Remote Similarity	NPD6684	Approved
0.6117	Remote Similarity	NPD5330	Approved
0.6117	Remote Similarity	NPD7521	Approved
0.6075	Remote Similarity	NPD8171	Discontinued
0.6064	Remote Similarity	NPD2687	Approved
0.6064	Remote Similarity	NPD2254	Approved
0.6064	Remote Similarity	NPD2686	Approved
0.6036	Remote Similarity	NPD6648	Approved
0.6032	Remote Similarity	NPD8293	Discontinued
0.602	Remote Similarity	NPD6116	Phase 1
0.6017	Remote Similarity	NPD6882	Approved
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD8513	Phase 3
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD6903	Approved
0.5982	Remote Similarity	NPD5344	Discontinued
0.598	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3669	Approved
0.5968	Remote Similarity	NPD6370	Approved
0.595	Remote Similarity	NPD7115	Discovery
0.595	Remote Similarity	NPD6009	Approved
0.5942	Remote Similarity	NPD7625	Phase 1
0.5941	Remote Similarity	NPD1780	Approved
0.5941	Remote Similarity	NPD1779	Approved
0.5922	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6067	Discontinued
0.5918	Remote Similarity	NPD6117	Approved
0.5913	Remote Similarity	NPD6402	Approved
0.5913	Remote Similarity	NPD6675	Approved
0.5913	Remote Similarity	NPD5739	Approved
0.5913	Remote Similarity	NPD7128	Approved
0.5905	Remote Similarity	NPD3573	Approved
0.5882	Remote Similarity	NPD6053	Discontinued
0.5873	Remote Similarity	NPD7492	Approved
0.5865	Remote Similarity	NPD1694	Approved
0.5833	Remote Similarity	NPD5693	Phase 1
0.5833	Remote Similarity	NPD7637	Suspended
0.5833	Remote Similarity	NPD5777	Approved
0.5827	Remote Similarity	NPD6616	Approved
0.5826	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6695	Phase 3
0.5818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7339	Approved
0.5816	Remote Similarity	NPD6942	Approved
0.5812	Remote Similarity	NPD7320	Approved
0.5812	Remote Similarity	NPD6881	Approved
0.5812	Remote Similarity	NPD6899	Approved
0.5806	Remote Similarity	NPD6059	Approved
0.5806	Remote Similarity	NPD6054	Approved
0.5781	Remote Similarity	NPD7078	Approved
0.5778	Remote Similarity	NPD1145	Discontinued
0.5769	Remote Similarity	NPD3668	Phase 3
0.5769	Remote Similarity	NPD4786	Approved
0.5763	Remote Similarity	NPD6373	Approved
0.5763	Remote Similarity	NPD6372	Approved
0.5758	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD3667	Approved
0.5726	Remote Similarity	NPD5697	Approved
0.5726	Remote Similarity	NPD5701	Approved
0.5714	Remote Similarity	NPD1810	Approved
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD1811	Approved
0.5702	Remote Similarity	NPD4632	Approved
0.5678	Remote Similarity	NPD6011	Approved
0.5676	Remote Similarity	NPD7991	Discontinued
0.5673	Remote Similarity	NPD4788	Approved
0.5667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6617	Approved
0.5667	Remote Similarity	NPD6869	Approved
0.5667	Remote Similarity	NPD6847	Approved
0.5667	Remote Similarity	NPD6650	Approved
0.5667	Remote Similarity	NPD6649	Approved
0.5667	Remote Similarity	NPD8130	Phase 1
0.5664	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6098	Approved
0.566	Remote Similarity	NPD3618	Phase 1
0.5648	Remote Similarity	NPD5328	Approved
0.5648	Remote Similarity	NPD6673	Approved
0.5648	Remote Similarity	NPD6904	Approved
0.5648	Remote Similarity	NPD6080	Approved
0.5648	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6921	Approved
0.5635	Remote Similarity	NPD6015	Approved
0.5635	Remote Similarity	NPD6016	Approved
0.563	Remote Similarity	NPD6014	Approved
0.563	Remote Similarity	NPD6013	Approved
0.563	Remote Similarity	NPD6012	Approved
0.562	Remote Similarity	NPD8297	Approved
0.561	Remote Similarity	NPD6940	Discontinued
0.5607	Remote Similarity	NPD7524	Approved
0.5607	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7750	Discontinued

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