NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1275.5
Volume:	1158.686
LogP:	-1.018
LogD:	-0.642
LogS:	-2.692
# Rotatable Bonds:	17
TPSA:	477.48
# H-Bond Aceptor:	31
# H-Bond Donor:	14
# Rings:	10
# Heavy Atoms:	32

MedChem Properties

QED Drug-Likeness Score:	0.037
Synthetic Accessibility Score:	7.53
Fsp3:	0.945
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.418
MDCK Permeability:	0.0006669888971373439
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.996
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	47.91280746459961%
Volume Distribution (VD):	-0.313
Pgp-substrate:	18.659582138061523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.23
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	0.037
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.63
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.552
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.476
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.517
Carcinogencity:	0.266
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC476672

Natural Product ID:	NPC476672
*Common Name:**	Astrosterioside C
IUPAC Name:	sodium;[(3S,5S,6S,8S,10S,13S,14S,17S)-17-acetyl-6-[(2R,3R,4S,5R,6R)-4-[(2S,3R,4S,5R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5S,6R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-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:	VHWNTAMECVIWOJ-HGPIJKDDSA-M
Standard InCHI:	InChI=1S/C55H88O31S.Na/c1-18(58)24-7-8-25-23-14-28(27-13-22(86-87(71,72)73)9-11-55(27,6)26(23)10-12-54(24,25)5)78-50-42(69)45(34(61)20(3)76-50)83-52-46(84-48-41(68)38(65)32(59)19(2)75-48)37(64)31(17-74-52)81-53-47(39(66)35(62)29(15-56)80-53)85-51-43(70)44(33(60)21(4)77-51)82-49-40(67)36(63)30(16-57)79-49;/h10,19-25,27-53,56-57,59-70H,7-9,11-17H2,1-6H3,(H,71,72,73);/q;+1/p-1/t19-,20-,21-,22+,23+,24-,25+,27-,28+,29-,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-;/m1./s1
SMILES:	C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](CO[C@H]2O[C@H]3[C@@H]([C@H](O[C@H]([C@@H]3O)O[C@H]4C[C@H]5[C@@H]6CC[C@@H]([C@]6(CC=C5[C@@]7([C@@H]4C[C@H](CC7)OS(=O)(=O)[O-])C)C)C(=O)C)C)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@H]([C@H](O9)C)O)O[C@H]1[C@@H]([C@H]([C@@H](O1)CO)O)O)O)O)O)O)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	73352261
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	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	50000	nM	PMID[24047259]
NPT2	Others	Unspecified		IC50	=	30490	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 NPC476672 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	285
0.1-0.2	1849
0.2-0.3	6116
0.3-0.4	13539
0.4-0.5	8936
0.5-0.6	5808
0.6-0.7	3616
0.7-0.8	1612
0.8-0.85	581
0.85-0.9	310
0.9-0.95	39
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC476674
0.9646	High Similarity	NPC476675
0.9558	High Similarity	NPC476670
0.9316	High Similarity	NPC476673
0.9204	High Similarity	NPC279638
0.9196	High Similarity	NPC476671
0.9098	High Similarity	NPC478069
0.9083	High Similarity	NPC477235
0.9068	High Similarity	NPC473505
0.906	High Similarity	NPC15918
0.906	High Similarity	NPC305771
0.906	High Similarity	NPC94072
0.906	High Similarity	NPC169816
0.8983	High Similarity	NPC256983
0.8974	High Similarity	NPC476544
0.8974	High Similarity	NPC476545
0.8974	High Similarity	NPC249553
0.8974	High Similarity	NPC476543
0.8974	High Similarity	NPC182900
0.8966	High Similarity	NPC197003
0.8966	High Similarity	NPC190939
0.8938	High Similarity	NPC210420
0.8938	High Similarity	NPC474265
0.8889	High Similarity	NPC308459
0.8889	High Similarity	NPC129393
0.8814	High Similarity	NPC477463
0.8803	High Similarity	NPC477464
0.8803	High Similarity	NPC161738
0.879	High Similarity	NPC477234
0.8783	High Similarity	NPC473882
0.8783	High Similarity	NPC473714
0.8783	High Similarity	NPC250247
0.8783	High Similarity	NPC227551
0.8783	High Similarity	NPC236638
0.8783	High Similarity	NPC43550
0.8783	High Similarity	NPC204414
0.8783	High Similarity	NPC4328
0.8783	High Similarity	NPC60557
0.8783	High Similarity	NPC67857
0.8783	High Similarity	NPC65105
0.8783	High Similarity	NPC476068
0.8783	High Similarity	NPC161717
0.8783	High Similarity	NPC261506
0.8783	High Similarity	NPC100639
0.8783	High Similarity	NPC76972
0.8783	High Similarity	NPC123199
0.8783	High Similarity	NPC475140
0.8783	High Similarity	NPC294453
0.8783	High Similarity	NPC298034
0.8783	High Similarity	NPC119592
0.8783	High Similarity	NPC305981
0.8783	High Similarity	NPC293330
0.8783	High Similarity	NPC71065
0.8783	High Similarity	NPC70809
0.8783	High Similarity	NPC309907
0.8783	High Similarity	NPC474557
0.8783	High Similarity	NPC471385
0.8783	High Similarity	NPC79643
0.8783	High Similarity	NPC57484
0.8783	High Similarity	NPC475160
0.8783	High Similarity	NPC471550
0.8783	High Similarity	NPC202828
0.8783	High Similarity	NPC224381
0.8783	High Similarity	NPC41061
0.8783	High Similarity	NPC469782
0.8783	High Similarity	NPC54636
0.8761	High Similarity	NPC52241
0.8761	High Similarity	NPC475317
0.8761	High Similarity	NPC154856
0.875	High Similarity	NPC248202
0.8718	High Similarity	NPC470514
0.8718	High Similarity	NPC470513
0.8718	High Similarity	NPC475899
0.8696	High Similarity	NPC473826
0.8696	High Similarity	NPC151543
0.8696	High Similarity	NPC155410
0.8696	High Similarity	NPC309714
0.8696	High Similarity	NPC475467
0.8696	High Similarity	NPC166422
0.8696	High Similarity	NPC251309
0.8696	High Similarity	NPC219180
0.8696	High Similarity	NPC114304
0.8696	High Similarity	NPC260665
0.8696	High Similarity	NPC475287
0.8696	High Similarity	NPC133818
0.8696	High Similarity	NPC323341
0.8696	High Similarity	NPC174720
0.8696	High Similarity	NPC192600
0.8696	High Similarity	NPC241909
0.8696	High Similarity	NPC251263
0.8696	High Similarity	NPC295823
0.8696	High Similarity	NPC114287
0.8696	High Similarity	NPC46665
0.8684	High Similarity	NPC285410
0.8684	High Similarity	NPC269466
0.8684	High Similarity	NPC263827
0.8684	High Similarity	NPC250481
0.8673	High Similarity	NPC302057
0.8667	High Similarity	NPC476542
0.8667	High Similarity	NPC228701
0.8661	High Similarity	NPC477233
0.8661	High Similarity	NPC477232
0.8655	High Similarity	NPC475182
0.8655	High Similarity	NPC68767
0.8655	High Similarity	NPC51099
0.8655	High Similarity	NPC293031
0.8655	High Similarity	NPC275225
0.8651	High Similarity	NPC477236
0.8644	High Similarity	NPC207738
0.8632	High Similarity	NPC475514
0.8632	High Similarity	NPC110633
0.8632	High Similarity	NPC220160
0.8632	High Similarity	NPC471580
0.8632	High Similarity	NPC470876
0.8632	High Similarity	NPC102505
0.8632	High Similarity	NPC85154
0.8632	High Similarity	NPC475209
0.8632	High Similarity	NPC33012
0.8632	High Similarity	NPC185466
0.8632	High Similarity	NPC69811
0.8632	High Similarity	NPC477807
0.8632	High Similarity	NPC191827
0.8632	High Similarity	NPC148417
0.8632	High Similarity	NPC473452
0.8632	High Similarity	NPC8524
0.8632	High Similarity	NPC104137
0.8632	High Similarity	NPC286457
0.8632	High Similarity	NPC309223
0.8632	High Similarity	NPC123522
0.8632	High Similarity	NPC136768
0.8621	High Similarity	NPC477810
0.8621	High Similarity	NPC477808
0.8621	High Similarity	NPC165439
0.8609	High Similarity	NPC276093
0.8609	High Similarity	NPC257468
0.8609	High Similarity	NPC263359
0.8609	High Similarity	NPC101744
0.8609	High Similarity	NPC233003
0.8609	High Similarity	NPC473373
0.8609	High Similarity	NPC475504
0.8609	High Similarity	NPC109079
0.8609	High Similarity	NPC130427
0.8609	High Similarity	NPC102439
0.8609	High Similarity	NPC469946
0.8609	High Similarity	NPC32361
0.8609	High Similarity	NPC31896
0.8609	High Similarity	NPC210569
0.8609	High Similarity	NPC292677
0.8609	High Similarity	NPC139044
0.8609	High Similarity	NPC324875
0.8609	High Similarity	NPC471383
0.8609	High Similarity	NPC475516
0.8609	High Similarity	NPC104400
0.8609	High Similarity	NPC10320
0.8609	High Similarity	NPC79718
0.8609	High Similarity	NPC104071
0.8609	High Similarity	NPC244431
0.8596	High Similarity	NPC477811
0.8596	High Similarity	NPC129340
0.8596	High Similarity	NPC101450
0.8596	High Similarity	NPC222202
0.8596	High Similarity	NPC269297
0.8596	High Similarity	NPC224314
0.8596	High Similarity	NPC87998
0.8596	High Similarity	NPC23808
0.8595	High Similarity	NPC473474
0.8584	High Similarity	NPC159005
0.8584	High Similarity	NPC6931
0.8584	High Similarity	NPC220427
0.8583	High Similarity	NPC131824
0.8571	High Similarity	NPC37860
0.8571	High Similarity	NPC475187
0.8571	High Similarity	NPC153673
0.8571	High Similarity	NPC95243
0.8571	High Similarity	NPC110385
0.8571	High Similarity	NPC267694
0.8571	High Similarity	NPC142151
0.8571	High Similarity	NPC144644
0.8571	High Similarity	NPC63023
0.8559	High Similarity	NPC237191
0.8559	High Similarity	NPC232237
0.8559	High Similarity	NPC105800
0.8559	High Similarity	NPC36831
0.8547	High Similarity	NPC476992
0.8547	High Similarity	NPC471384
0.8547	High Similarity	NPC63609
0.8547	High Similarity	NPC472718
0.8547	High Similarity	NPC288205
0.8547	High Similarity	NPC244127
0.8547	High Similarity	NPC75287
0.8547	High Similarity	NPC26626
0.8547	High Similarity	NPC51465
0.8547	High Similarity	NPC305267
0.8547	High Similarity	NPC161674
0.8534	High Similarity	NPC73318
0.8534	High Similarity	NPC477074
0.8534	High Similarity	NPC150400
0.8534	High Similarity	NPC124296
0.8534	High Similarity	NPC163183
0.8534	High Similarity	NPC79900

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 NPC476672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	2076
0.2-0.3	4311
0.3-0.4	1669
0.4-0.5	445
0.5-0.6	246
0.6-0.7	124
0.7-0.8	38
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
0.8174	Intermediate Similarity	NPD6412	Phase 2
0.8067	Intermediate Similarity	NPD8133	Approved
0.8034	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD8328	Phase 3
0.7845	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD8377	Approved
0.7823	Intermediate Similarity	NPD8294	Approved
0.776	Intermediate Similarity	NPD8296	Approved
0.776	Intermediate Similarity	NPD8380	Approved
0.776	Intermediate Similarity	NPD8378	Approved
0.776	Intermediate Similarity	NPD8335	Approved
0.776	Intermediate Similarity	NPD8379	Approved
0.7698	Intermediate Similarity	NPD6370	Approved
0.7674	Intermediate Similarity	NPD7736	Approved
0.7656	Intermediate Similarity	NPD7507	Approved
0.7619	Intermediate Similarity	NPD8033	Approved
0.7597	Intermediate Similarity	NPD8293	Discontinued
0.7581	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6059	Approved
0.754	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6067	Discontinued
0.7481	Intermediate Similarity	NPD7319	Approved
0.7381	Intermediate Similarity	NPD7327	Approved
0.7381	Intermediate Similarity	NPD7328	Approved
0.7355	Intermediate Similarity	NPD6686	Approved
0.7344	Intermediate Similarity	NPD8516	Approved
0.7344	Intermediate Similarity	NPD8517	Approved
0.7344	Intermediate Similarity	NPD6015	Approved
0.7344	Intermediate Similarity	NPD6016	Approved
0.7344	Intermediate Similarity	NPD8515	Approved
0.7323	Intermediate Similarity	NPD7516	Approved
0.7308	Intermediate Similarity	NPD7492	Approved
0.7287	Intermediate Similarity	NPD5988	Approved
0.7281	Intermediate Similarity	NPD8171	Discontinued
0.7252	Intermediate Similarity	NPD6616	Approved
0.7209	Intermediate Similarity	NPD8513	Phase 3
0.7209	Intermediate Similarity	NPD7503	Approved
0.7197	Intermediate Similarity	NPD7078	Approved
0.7132	Intermediate Similarity	NPD8450	Suspended
0.712	Intermediate Similarity	NPD8297	Approved
0.712	Intermediate Similarity	NPD6882	Approved
0.7059	Intermediate Similarity	NPD8449	Approved
0.704	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6009	Approved
0.7015	Intermediate Similarity	NPD6033	Approved
0.7	Intermediate Similarity	NPD6319	Approved
0.6983	Remote Similarity	NPD6399	Phase 3
0.6935	Remote Similarity	NPD7320	Approved
0.6929	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD7748	Approved
0.6911	Remote Similarity	NPD6675	Approved
0.6911	Remote Similarity	NPD7128	Approved
0.6911	Remote Similarity	NPD5739	Approved
0.6911	Remote Similarity	NPD6402	Approved
0.6891	Remote Similarity	NPD7902	Approved
0.688	Remote Similarity	NPD6373	Approved
0.688	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD4786	Approved
0.687	Remote Similarity	NPD5328	Approved
0.68	Remote Similarity	NPD6899	Approved
0.68	Remote Similarity	NPD6881	Approved
0.6774	Remote Similarity	NPD6008	Approved
0.6772	Remote Similarity	NPD8130	Phase 1
0.6772	Remote Similarity	NPD6649	Approved
0.6772	Remote Similarity	NPD6650	Approved
0.6769	Remote Similarity	NPD7115	Discovery
0.6754	Remote Similarity	NPD3618	Phase 1
0.6752	Remote Similarity	NPD6079	Approved
0.6752	Remote Similarity	NPD8035	Phase 2
0.6752	Remote Similarity	NPD8034	Phase 2
0.6752	Remote Similarity	NPD7515	Phase 2
0.675	Remote Similarity	NPD4755	Approved
0.6726	Remote Similarity	NPD3668	Phase 3
0.672	Remote Similarity	NPD5697	Approved
0.672	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD3667	Approved
0.6695	Remote Similarity	NPD4202	Approved
0.6694	Remote Similarity	NPD7638	Approved
0.6693	Remote Similarity	NPD6883	Approved
0.6693	Remote Similarity	NPD7290	Approved
0.6693	Remote Similarity	NPD4634	Approved
0.6693	Remote Similarity	NPD7102	Approved
0.6641	Remote Similarity	NPD6869	Approved
0.6641	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6847	Approved
0.6641	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4696	Approved
0.6639	Remote Similarity	NPD7900	Approved
0.6639	Remote Similarity	NPD5285	Approved
0.6639	Remote Similarity	NPD7640	Approved
0.6639	Remote Similarity	NPD4700	Approved
0.6639	Remote Similarity	NPD5286	Approved
0.6639	Remote Similarity	NPD7639	Approved
0.6614	Remote Similarity	NPD6014	Approved
0.6614	Remote Similarity	NPD6012	Approved
0.6614	Remote Similarity	NPD6013	Approved
0.6612	Remote Similarity	NPD6083	Phase 2
0.6612	Remote Similarity	NPD6084	Phase 2
0.6593	Remote Similarity	NPD7604	Phase 2
0.6567	Remote Similarity	NPD5983	Phase 2
0.6547	Remote Similarity	NPD5956	Approved
0.6535	Remote Similarity	NPD6011	Approved
0.6532	Remote Similarity	NPD5224	Approved
0.6532	Remote Similarity	NPD5226	Approved
0.6532	Remote Similarity	NPD5225	Approved
0.6532	Remote Similarity	NPD4633	Approved
0.6532	Remote Similarity	NPD5211	Phase 2
0.6529	Remote Similarity	NPD5221	Approved
0.6529	Remote Similarity	NPD4697	Phase 3
0.6529	Remote Similarity	NPD5222	Approved
0.6529	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD4768	Approved
0.6508	Remote Similarity	NPD4767	Approved
0.6496	Remote Similarity	NPD6336	Discontinued
0.6484	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5175	Approved
0.648	Remote Similarity	NPD5174	Approved
0.648	Remote Similarity	NPD4754	Approved
0.6475	Remote Similarity	NPD5173	Approved
0.6452	Remote Similarity	NPD5223	Approved
0.6446	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4753	Phase 2
0.6435	Remote Similarity	NPD3665	Phase 1
0.6435	Remote Similarity	NPD3666	Approved
0.6435	Remote Similarity	NPD3133	Approved
0.6429	Remote Similarity	NPD5141	Approved
0.6406	Remote Similarity	NPD4729	Approved
0.6406	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4730	Approved
0.6403	Remote Similarity	NPD8336	Approved
0.6403	Remote Similarity	NPD8337	Approved
0.6372	Remote Similarity	NPD7525	Registered
0.6356	Remote Similarity	NPD6672	Approved
0.6356	Remote Similarity	NPD5737	Approved
0.6356	Remote Similarity	NPD6903	Approved
0.6356	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7625	Phase 1
0.6331	Remote Similarity	NPD8074	Phase 3
0.6325	Remote Similarity	NPD5330	Approved
0.6325	Remote Similarity	NPD7334	Approved
0.6325	Remote Similarity	NPD7146	Approved
0.6325	Remote Similarity	NPD6409	Approved
0.6325	Remote Similarity	NPD7521	Approved
0.6325	Remote Similarity	NPD6684	Approved
0.6324	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6274	Approved
0.6311	Remote Similarity	NPD5695	Phase 3
0.6308	Remote Similarity	NPD5251	Approved
0.6308	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5250	Approved
0.6308	Remote Similarity	NPD5248	Approved
0.6308	Remote Similarity	NPD5249	Phase 3
0.6308	Remote Similarity	NPD5247	Approved
0.6296	Remote Similarity	NPD7101	Approved
0.6296	Remote Similarity	NPD7100	Approved
0.629	Remote Similarity	NPD5696	Approved
0.6283	Remote Similarity	NPD7645	Phase 2
0.6279	Remote Similarity	NPD5128	Approved
0.6269	Remote Similarity	NPD6317	Approved
0.6228	Remote Similarity	NPD6928	Phase 2
0.6224	Remote Similarity	NPD8338	Approved
0.6222	Remote Similarity	NPD6335	Approved
0.6204	Remote Similarity	NPD6908	Approved
0.6204	Remote Similarity	NPD6909	Approved
0.6194	Remote Similarity	NPD6940	Discontinued
0.6194	Remote Similarity	NPD6868	Approved
0.6186	Remote Similarity	NPD5279	Phase 3
0.6183	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5135	Approved
0.6179	Remote Similarity	NPD4629	Approved
0.6179	Remote Similarity	NPD5210	Approved
0.616	Remote Similarity	NPD4225	Approved
0.6142	Remote Similarity	NPD7632	Discontinued
0.6136	Remote Similarity	NPD5216	Approved
0.6136	Remote Similarity	NPD5215	Approved
0.6136	Remote Similarity	NPD5217	Approved
0.6134	Remote Similarity	NPD7524	Approved
0.6121	Remote Similarity	NPD4223	Phase 3
0.6121	Remote Similarity	NPD4221	Approved
0.6103	Remote Similarity	NPD6313	Approved
0.6103	Remote Similarity	NPD6314	Approved
0.6102	Remote Similarity	NPD5329	Approved
0.6098	Remote Similarity	NPD6001	Approved
0.609	Remote Similarity	NPD6053	Discontinued
0.6077	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7339	Approved
0.6071	Remote Similarity	NPD6942	Approved
0.6066	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD5169	Approved
0.6053	Remote Similarity	NPD6697	Approved
0.6053	Remote Similarity	NPD6115	Approved
0.6053	Remote Similarity	NPD6118	Approved
0.6053	Remote Similarity	NPD6114	Approved
0.605	Remote Similarity	NPD6098	Approved
0.605	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6904	Approved
0.6033	Remote Similarity	NPD6673	Approved
0.6033	Remote Similarity	NPD6080	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