NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1257.52
Volume:	1164.322
LogP:	0.386
LogD:	-0.074
LogS:	-2.899
# Rotatable Bonds:	18
TPSA:	455.86
# H-Bond Aceptor:	29
# H-Bond Donor:	13
# Rings:	9
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.027
Synthetic Accessibility Score:	7.489
Fsp3:	0.929
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.325
MDCK Permeability:	0.0003891747328452766
Pgp-inhibitor:	0.071
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.286
Plasma Protein Binding (PPB):	48.730289459228516%
Volume Distribution (VD):	-0.188
Pgp-substrate:	19.83990478515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.313
Half-life (T1/2):	0.698

ADMET: Toxicity

hERG Blockers:	0.383
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.804
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.82
Carcinogencity:	0.376
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.994

Download Data

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

Natural Product: NPC476673

Natural Product ID:	NPC476673
*Common Name:**	sodium;[(3S,5S,6S,8S,10S,13S,14S,17S)-6-[(2R,3R,4S,5R,6R)-4-[(2S,3R,4S,5S,6R)-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R)-2-hydroxy-4,6-dioxoheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
IUPAC Name:	sodium;[(3S,5S,6S,8S,10S,13S,14S,17S)-6-[(2R,3R,4S,5R,6R)-4-[(2S,3R,4S,5S,6R)-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-[(2R)-2-hydroxy-4,6-dioxoheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
Synonyms:
Standard InCHIKey:	ZLQYLBIYSFRNLT-IZUBAVJXSA-M
Standard InCHI:	InChI=1S/C56H90O29S.Na/c1-20(58)15-25(59)18-56(8,71)33-10-9-28-27-17-31(30-16-26(85-86(72,73)74)11-13-54(30,6)29(27)12-14-55(28,33)7)79-51-44(70)46(37(63)32(19-57)80-51)82-53-48(84-50-42(68)39(65)35(61)22(3)76-50)43(69)45(24(5)78-53)81-52-47(40(66)36(62)23(4)77-52)83-49-41(67)38(64)34(60)21(2)75-49;/h12,21-24,26-28,30-53,57,60-71H,9-11,13-19H2,1-8H3,(H,72,73,74);/q;+1/p-1/t21-,22-,23-,24-,26+,27+,28+,30-,31+,32-,33+,34+,35-,36+,37-,38+,39+,40+,41-,42-,43+,44-,45-,46+,47-,48-,49+,50+,51-,52+,53+,54-,55+,56-;/m1./s1
SMILES:	C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C)O)O)O)O[C@H]5[C@@H]([C@H](O[C@H]([C@@H]5O)O[C@H]6C[C@H]7[C@@H]8CC[C@@H]([C@]8(CC=C7[C@@]9([C@@H]6C[C@H](CC9)OS(=O)(=O)[O-])C)C)[C@@](C)(CC(=O)CC(=O)C)O)CO)O)C)C)O)O)O)O)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	73346140
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33624	Astropecten monacanthus	Species	Astropectinidae	Eukaryota	n.a.	Cat Ba, Haiphong, Vietnam	2012-JUN	PMID[24047259]

☑ 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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	=	3510	nM	PMID[24047259]
NPT2	Others	Unspecified	IC50	=	1210	nM	PMID[24047259]
NPT2	Others	Unspecified	IC50	=	600	nM	PMID[24047259]

☑ 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 NPC476673 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	294
0.1-0.2	2001
0.2-0.3	6024
0.3-0.4	11835
0.4-0.5	10117
0.5-0.6	6076
0.6-0.7	3763
0.7-0.8	1640
0.8-0.85	687
0.85-0.9	242
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9573	High Similarity	NPC476674
0.9316	High Similarity	NPC476675
0.9316	High Similarity	NPC476672
0.9268	High Similarity	NPC478069
0.9052	High Similarity	NPC279638
0.896	High Similarity	NPC477234
0.8943	High Similarity	NPC477235
0.8926	High Similarity	NPC248202
0.8908	High Similarity	NPC476670
0.8833	High Similarity	NPC475182
0.8828	High Similarity	NPC477233
0.8828	High Similarity	NPC477232
0.8824	High Similarity	NPC190939
0.8824	High Similarity	NPC197003
0.8819	High Similarity	NPC477236
0.8793	High Similarity	NPC210420
0.8793	High Similarity	NPC474265
0.877	High Similarity	NPC473505
0.877	High Similarity	NPC473474
0.876	High Similarity	NPC305771
0.876	High Similarity	NPC169816
0.876	High Similarity	NPC94072
0.876	High Similarity	NPC15918
0.875	High Similarity	NPC476991
0.875	High Similarity	NPC475187
0.875	High Similarity	NPC129393
0.8739	High Similarity	NPC470514
0.8739	High Similarity	NPC470513
0.8718	High Similarity	NPC476671
0.8689	High Similarity	NPC160084
0.8678	High Similarity	NPC249553
0.8678	High Similarity	NPC68767
0.8678	High Similarity	NPC182900
0.8678	High Similarity	NPC51099
0.8678	High Similarity	NPC293031
0.8678	High Similarity	NPC275225
0.8667	High Similarity	NPC135849
0.8667	High Similarity	NPC471577
0.8667	High Similarity	NPC25663
0.8667	High Similarity	NPC51564
0.8655	High Similarity	NPC475514
0.8655	High Similarity	NPC475209
0.8655	High Similarity	NPC85154
0.8655	High Similarity	NPC471580
0.8655	High Similarity	NPC470876
0.8655	High Similarity	NPC220160
0.8655	High Similarity	NPC123522
0.8655	High Similarity	NPC33012
0.8655	High Similarity	NPC191827
0.8655	High Similarity	NPC286457
0.8655	High Similarity	NPC309223
0.8655	High Similarity	NPC102505
0.8655	High Similarity	NPC473452
0.8655	High Similarity	NPC104137
0.8655	High Similarity	NPC8524
0.8655	High Similarity	NPC69811
0.8644	High Similarity	NPC473882
0.8644	High Similarity	NPC474557
0.8629	High Similarity	NPC292290
0.8621	High Similarity	NPC475317
0.8621	High Similarity	NPC52241
0.8621	High Similarity	NPC154856
0.8618	High Similarity	NPC130229
0.8607	High Similarity	NPC156789
0.8595	High Similarity	NPC37860
0.8595	High Similarity	NPC144644
0.8595	High Similarity	NPC110385
0.8595	High Similarity	NPC267694
0.8595	High Similarity	NPC153673
0.8595	High Similarity	NPC142151
0.8595	High Similarity	NPC308459
0.8583	High Similarity	NPC102015
0.8583	High Similarity	NPC237191
0.8583	High Similarity	NPC475632
0.8583	High Similarity	NPC86020
0.8571	High Similarity	NPC75287
0.8571	High Similarity	NPC26626
0.8571	High Similarity	NPC305267
0.8571	High Similarity	NPC476992
0.8571	High Similarity	NPC288205
0.8571	High Similarity	NPC51465
0.8548	High Similarity	NPC104427
0.8548	High Similarity	NPC181066
0.8548	High Similarity	NPC470218
0.8548	High Similarity	NPC469947
0.8537	High Similarity	NPC258617
0.8537	High Similarity	NPC200049
0.8537	High Similarity	NPC283417
0.8537	High Similarity	NPC228701
0.8537	High Similarity	NPC302543
0.8534	High Similarity	NPC302057
0.8512	High Similarity	NPC477464
0.8512	High Similarity	NPC207738
0.8512	High Similarity	NPC473386
0.8512	High Similarity	NPC161738
0.8504	High Similarity	NPC473805
0.8504	High Similarity	NPC473519
0.85	High Similarity	NPC473824
0.85	High Similarity	NPC475119
0.8487	Intermediate Similarity	NPC41061
0.8487	Intermediate Similarity	NPC469782
0.8487	Intermediate Similarity	NPC79643
0.8487	Intermediate Similarity	NPC298034
0.8487	Intermediate Similarity	NPC67857
0.8487	Intermediate Similarity	NPC476068
0.8487	Intermediate Similarity	NPC60557
0.8487	Intermediate Similarity	NPC236638
0.8487	Intermediate Similarity	NPC76972
0.8487	Intermediate Similarity	NPC123199
0.8487	Intermediate Similarity	NPC70809
0.8487	Intermediate Similarity	NPC471385
0.8487	Intermediate Similarity	NPC294453
0.8487	Intermediate Similarity	NPC202828
0.8487	Intermediate Similarity	NPC305981
0.8487	Intermediate Similarity	NPC65105
0.8487	Intermediate Similarity	NPC71065
0.8487	Intermediate Similarity	NPC57484
0.8487	Intermediate Similarity	NPC224381
0.8487	Intermediate Similarity	NPC227551
0.8487	Intermediate Similarity	NPC116024
0.8487	Intermediate Similarity	NPC475160
0.8487	Intermediate Similarity	NPC475140
0.8487	Intermediate Similarity	NPC473714
0.8487	Intermediate Similarity	NPC471550
0.8487	Intermediate Similarity	NPC261506
0.8487	Intermediate Similarity	NPC250247
0.8487	Intermediate Similarity	NPC119592
0.8487	Intermediate Similarity	NPC204414
0.8487	Intermediate Similarity	NPC4328
0.8487	Intermediate Similarity	NPC43550
0.8487	Intermediate Similarity	NPC293330
0.8487	Intermediate Similarity	NPC54636
0.8487	Intermediate Similarity	NPC161717
0.8487	Intermediate Similarity	NPC100639
0.8487	Intermediate Similarity	NPC309907
0.8487	Intermediate Similarity	NPC475486
0.8487	Intermediate Similarity	NPC164389
0.8475	Intermediate Similarity	NPC130427
0.8468	Intermediate Similarity	NPC33068
0.8455	Intermediate Similarity	NPC131469
0.8455	Intermediate Similarity	NPC162574
0.8455	Intermediate Similarity	NPC4749
0.8455	Intermediate Similarity	NPC313110
0.8455	Intermediate Similarity	NPC236870
0.8455	Intermediate Similarity	NPC80986
0.8455	Intermediate Similarity	NPC131824
0.8455	Intermediate Similarity	NPC10607
0.8455	Intermediate Similarity	NPC21691
0.8455	Intermediate Similarity	NPC187290
0.8455	Intermediate Similarity	NPC475591
0.8448	Intermediate Similarity	NPC159005
0.8448	Intermediate Similarity	NPC6931
0.8443	Intermediate Similarity	NPC473645
0.843	Intermediate Similarity	NPC36831
0.843	Intermediate Similarity	NPC475899
0.843	Intermediate Similarity	NPC473459
0.843	Intermediate Similarity	NPC105800
0.843	Intermediate Similarity	NPC232237
0.8417	Intermediate Similarity	NPC37134
0.8417	Intermediate Similarity	NPC291903
0.8417	Intermediate Similarity	NPC472718
0.8413	Intermediate Similarity	NPC470476
0.8403	Intermediate Similarity	NPC114304
0.8403	Intermediate Similarity	NPC114287
0.8403	Intermediate Similarity	NPC219180
0.8403	Intermediate Similarity	NPC260665
0.8403	Intermediate Similarity	NPC155410
0.8403	Intermediate Similarity	NPC192600
0.8403	Intermediate Similarity	NPC166422
0.8403	Intermediate Similarity	NPC151543
0.8403	Intermediate Similarity	NPC475287
0.8403	Intermediate Similarity	NPC475467
0.8403	Intermediate Similarity	NPC477074
0.8403	Intermediate Similarity	NPC241909
0.8403	Intermediate Similarity	NPC295823
0.8403	Intermediate Similarity	NPC251309
0.8403	Intermediate Similarity	NPC473826
0.8403	Intermediate Similarity	NPC174720
0.8403	Intermediate Similarity	NPC46665
0.8403	Intermediate Similarity	NPC309714
0.8403	Intermediate Similarity	NPC323341
0.8403	Intermediate Similarity	NPC133818
0.8403	Intermediate Similarity	NPC251263
0.8403	Intermediate Similarity	NPC146563
0.84	Intermediate Similarity	NPC475368
0.839	Intermediate Similarity	NPC263827
0.839	Intermediate Similarity	NPC250481
0.839	Intermediate Similarity	NPC285410
0.839	Intermediate Similarity	NPC269466
0.8387	Intermediate Similarity	NPC256983
0.8387	Intermediate Similarity	NPC281148
0.8387	Intermediate Similarity	NPC30735
0.8387	Intermediate Similarity	NPC257211
0.8387	Intermediate Similarity	NPC235405
0.8374	Intermediate Similarity	NPC476543
0.8374	Intermediate Similarity	NPC223301
0.8374	Intermediate Similarity	NPC301449
0.8374	Intermediate Similarity	NPC297263
0.8374	Intermediate Similarity	NPC62725
0.8374	Intermediate Similarity	NPC470478

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 NPC476673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	2190
0.2-0.3	4183
0.3-0.4	1640
0.4-0.5	461
0.5-0.6	253
0.6-0.7	134
0.7-0.8	35
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.824	Intermediate Similarity	NPD8328	Phase 3
0.7951	Intermediate Similarity	NPD8133	Approved
0.7903	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD6412	Phase 2
0.7874	Intermediate Similarity	NPD6370	Approved
0.7846	Intermediate Similarity	NPD7736	Approved
0.7786	Intermediate Similarity	NPD7319	Approved
0.7769	Intermediate Similarity	NPD8293	Discontinued
0.7769	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6054	Approved
0.7717	Intermediate Similarity	NPD6059	Approved
0.7692	Intermediate Similarity	NPD7507	Approved
0.7656	Intermediate Similarity	NPD8517	Approved
0.7656	Intermediate Similarity	NPD8515	Approved
0.7656	Intermediate Similarity	NPD8516	Approved
0.7583	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD8377	Approved
0.7578	Intermediate Similarity	NPD8294	Approved
0.7519	Intermediate Similarity	NPD8378	Approved
0.7519	Intermediate Similarity	NPD8513	Phase 3
0.7519	Intermediate Similarity	NPD8296	Approved
0.7519	Intermediate Similarity	NPD8380	Approved
0.7519	Intermediate Similarity	NPD6015	Approved
0.7519	Intermediate Similarity	NPD6016	Approved
0.7519	Intermediate Similarity	NPD8335	Approved
0.7519	Intermediate Similarity	NPD8379	Approved
0.7481	Intermediate Similarity	NPD7492	Approved
0.7462	Intermediate Similarity	NPD5988	Approved
0.7442	Intermediate Similarity	NPD6319	Approved
0.7424	Intermediate Similarity	NPD6616	Approved
0.7385	Intermediate Similarity	NPD8033	Approved
0.7368	Intermediate Similarity	NPD7078	Approved
0.7302	Intermediate Similarity	NPD6882	Approved
0.7302	Intermediate Similarity	NPD8297	Approved
0.7209	Intermediate Similarity	NPD6009	Approved
0.7185	Intermediate Similarity	NPD6033	Approved
0.7154	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7121	Intermediate Similarity	NPD7503	Approved
0.712	Intermediate Similarity	NPD6686	Approved
0.7109	Intermediate Similarity	NPD4632	Approved
0.7099	Intermediate Similarity	NPD7516	Approved
0.7097	Intermediate Similarity	NPD7128	Approved
0.7097	Intermediate Similarity	NPD5739	Approved
0.7097	Intermediate Similarity	NPD6675	Approved
0.7097	Intermediate Similarity	NPD6402	Approved
0.7063	Intermediate Similarity	NPD6373	Approved
0.7063	Intermediate Similarity	NPD6372	Approved
0.7015	Intermediate Similarity	NPD6067	Discontinued
0.6984	Remote Similarity	NPD6899	Approved
0.6984	Remote Similarity	NPD6881	Approved
0.6984	Remote Similarity	NPD7320	Approved
0.6953	Remote Similarity	NPD6650	Approved
0.6953	Remote Similarity	NPD6649	Approved
0.6953	Remote Similarity	NPD8130	Phase 1
0.6947	Remote Similarity	NPD7115	Discovery
0.6942	Remote Similarity	NPD4755	Approved
0.6923	Remote Similarity	NPD5328	Approved
0.6905	Remote Similarity	NPD5697	Approved
0.6905	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD7102	Approved
0.6875	Remote Similarity	NPD7290	Approved
0.685	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4700	Approved
0.6829	Remote Similarity	NPD4696	Approved
0.6829	Remote Similarity	NPD5285	Approved
0.6829	Remote Similarity	NPD5286	Approved
0.6822	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6847	Approved
0.6807	Remote Similarity	NPD6079	Approved
0.6797	Remote Similarity	NPD6012	Approved
0.6797	Remote Similarity	NPD6013	Approved
0.6797	Remote Similarity	NPD6014	Approved
0.6765	Remote Similarity	NPD7604	Phase 2
0.675	Remote Similarity	NPD8171	Discontinued
0.675	Remote Similarity	NPD6399	Phase 3
0.6741	Remote Similarity	NPD5983	Phase 2
0.672	Remote Similarity	NPD5211	Phase 2
0.672	Remote Similarity	NPD5225	Approved
0.672	Remote Similarity	NPD5226	Approved
0.672	Remote Similarity	NPD4633	Approved
0.672	Remote Similarity	NPD5224	Approved
0.6719	Remote Similarity	NPD6011	Approved
0.6694	Remote Similarity	NPD7748	Approved
0.6693	Remote Similarity	NPD6008	Approved
0.6693	Remote Similarity	NPD4768	Approved
0.6693	Remote Similarity	NPD4767	Approved
0.669	Remote Similarity	NPD8450	Suspended
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.664	Remote Similarity	NPD5223	Approved
0.6638	Remote Similarity	NPD4786	Approved
0.662	Remote Similarity	NPD8449	Approved
0.6619	Remote Similarity	NPD8074	Phase 3
0.6614	Remote Similarity	NPD5141	Approved
0.6612	Remote Similarity	NPD4202	Approved
0.6589	Remote Similarity	NPD4729	Approved
0.6589	Remote Similarity	NPD4730	Approved
0.6585	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5222	Approved
0.6585	Remote Similarity	NPD5221	Approved
0.6585	Remote Similarity	NPD4697	Phase 3
0.6532	Remote Similarity	NPD5173	Approved
0.6532	Remote Similarity	NPD6083	Phase 2
0.6532	Remote Similarity	NPD6084	Phase 2
0.6529	Remote Similarity	NPD7515	Phase 2
0.6529	Remote Similarity	NPD8034	Phase 2
0.6529	Remote Similarity	NPD8035	Phase 2
0.6525	Remote Similarity	NPD3618	Phase 1
0.6496	Remote Similarity	NPD3668	Phase 3
0.6493	Remote Similarity	NPD6274	Approved
0.6489	Remote Similarity	NPD5250	Approved
0.6489	Remote Similarity	NPD5248	Approved
0.6489	Remote Similarity	NPD5249	Phase 3
0.6489	Remote Similarity	NPD5251	Approved
0.6489	Remote Similarity	NPD5247	Approved
0.648	Remote Similarity	NPD7638	Approved
0.6479	Remote Similarity	NPD5956	Approved
0.6471	Remote Similarity	NPD7101	Approved
0.6471	Remote Similarity	NPD7100	Approved
0.6466	Remote Similarity	NPD3667	Approved
0.6462	Remote Similarity	NPD5128	Approved
0.6454	Remote Similarity	NPD8336	Approved
0.6454	Remote Similarity	NPD8337	Approved
0.6444	Remote Similarity	NPD6317	Approved
0.6429	Remote Similarity	NPD7639	Approved
0.6429	Remote Similarity	NPD7640	Approved
0.6423	Remote Similarity	NPD7900	Approved
0.6423	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6335	Approved
0.6393	Remote Similarity	NPD6411	Approved
0.6377	Remote Similarity	NPD6908	Approved
0.6377	Remote Similarity	NPD6921	Approved
0.6377	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5135	Approved
0.6316	Remote Similarity	NPD5216	Approved
0.6316	Remote Similarity	NPD5217	Approved
0.6316	Remote Similarity	NPD5215	Approved
0.6303	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7525	Registered
0.6277	Remote Similarity	NPD6313	Approved
0.6277	Remote Similarity	NPD6314	Approved
0.6276	Remote Similarity	NPD8338	Approved
0.6259	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD5169	Approved
0.624	Remote Similarity	NPD5695	Phase 3
0.623	Remote Similarity	NPD6101	Approved
0.623	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5696	Approved
0.6218	Remote Similarity	NPD3666	Approved
0.6218	Remote Similarity	NPD3665	Phase 1
0.6218	Remote Similarity	NPD3133	Approved
0.6204	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD3573	Approved
0.6194	Remote Similarity	NPD5127	Approved
0.6169	Remote Similarity	NPD7625	Phase 1
0.6148	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5737	Approved
0.6148	Remote Similarity	NPD6053	Discontinued
0.6148	Remote Similarity	NPD6672	Approved
0.6143	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7983	Approved
0.6116	Remote Similarity	NPD6409	Approved
0.6116	Remote Similarity	NPD7146	Approved
0.6116	Remote Similarity	NPD7334	Approved
0.6116	Remote Similarity	NPD5330	Approved
0.6116	Remote Similarity	NPD6684	Approved
0.6116	Remote Similarity	NPD7521	Approved
0.6115	Remote Similarity	NPD4522	Approved
0.6111	Remote Similarity	NPD5210	Approved
0.6111	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4629	Approved
0.6099	Remote Similarity	NPD8080	Discontinued
0.6095	Remote Similarity	NPD7799	Discontinued
0.6094	Remote Similarity	NPD4225	Approved
0.609	Remote Similarity	NPD5168	Approved
0.608	Remote Similarity	NPD5778	Approved
0.608	Remote Similarity	NPD5779	Approved
0.6068	Remote Similarity	NPD7645	Phase 2
0.6066	Remote Similarity	NPD7524	Approved
0.6058	Remote Similarity	NPD5167	Approved
0.605	Remote Similarity	NPD4223	Phase 3
0.605	Remote Similarity	NPD4221	Approved
0.6042	Remote Similarity	NPD8448	Approved
0.6033	Remote Similarity	NPD5329	Approved
0.6028	Remote Similarity	NPD8444	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