NPASS Compound

Structure

NPC272576 OpenBabel07101718302D 34 37 0 0 1 0 0 0 0 0999 V2000 7.5032 0.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6996 0.1066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7961 1.3569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 0.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3660 2.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 3.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8301 1.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2321 2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -0.4019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 4.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 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 1 5 2 0 0 0 0 5 24 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 10 16 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 26 1 0 0 0 0 13 33 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 25 1 0 0 0 0 16 28 2 0 0 0 0 17 12 1 6 0 0 0 17 20 1 0 0 0 0 17 34 1 0 0 0 0 18 25 1 1 0 0 0 18 26 1 0 0 0 0 19 26 1 1 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 31 1 1 0 0 0 22 23 1 0 0 0 0 22 32 1 6 0 0 0 23 33 1 6 0 0 0 23 34 1 0 0 0 0 24 2 1 1 0 0 0 25 3 1 1 0 0 0 26 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.27
Volume:	486.439
LogP:	1.469
LogD:	1.427
LogS:	-2.193
# Rotatable Bonds:	5
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	5.27
Fsp3:	0.808
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.447
MDCK Permeability:	7.042360266495962e-06
Pgp-inhibitor:	0.081
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.165
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.186

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	49.21892547607422%
Volume Distribution (VD):	0.609
Pgp-substrate:	40.61571502685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.773
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.535
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	2.201
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.437
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.027
Carcinogencity:	0.615
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC272576

Natural Product ID:	NPC272576
*Common Name:**	Virescenoside P
IUPAC Name:	(1S,2S,4aS,7S,10aR)-7-ethenyl-2-hydroxy-1,4a,7-trimethyl-1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4,5,6,8,10,10a-octahydrophenanthren-9-one
Synonyms:	virescenoside P
Standard InCHIKey:	XYQOVSKSRKWGQS-MTRKJMMMSA-N
Standard InCHI:	InChI=1S/C26H40O8/c1-5-24(2)8-6-15-14(11-24)16(28)10-18-25(15,3)9-7-19(29)26(18,4)13-33-23-22(32)21(31)20(30)17(12-27)34-23/h5,17-23,27,29-32H,1,6-13H2,2-4H3/t17-,18-,19+,20-,21-,22+,23-,24+,25-,26-/m1/s1
SMILES:	C=C[C@@]1(C)CCC2=C(C1)C(=O)C[C@@H]1[C@]2(C)CC[C@@H]([C@]1(C)CO[C@H]1[C@H]([C@@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465083
PubChem CID:	21672035
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene 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
NPO32826	acremonium striatisporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[12027733]

☑ 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	1
MIC	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20000.0	nM	PMID[491858]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	5000.0	nM	PMID[491858]

☑ 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 NPC272576 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	235
0.1-0.2	1435
0.2-0.3	4519
0.3-0.4	7944
0.4-0.5	12762
0.5-0.6	7797
0.6-0.7	5415
0.7-0.8	2400
0.8-0.85	169
0.85-0.9	18
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9151	High Similarity	NPC62696
0.9151	High Similarity	NPC293038
0.9065	High Similarity	NPC102088
0.8991	High Similarity	NPC176005
0.8899	High Similarity	NPC309433
0.8879	High Similarity	NPC471967
0.8857	High Similarity	NPC473288
0.8812	High Similarity	NPC70733
0.8812	High Similarity	NPC56071
0.8796	High Similarity	NPC260665
0.8774	High Similarity	NPC137917
0.875	High Similarity	NPC202051
0.8739	High Similarity	NPC473401
0.87	High Similarity	NPC108141
0.8692	High Similarity	NPC78046
0.8692	High Similarity	NPC129340
0.8692	High Similarity	NPC269095
0.8692	High Similarity	NPC220984
0.8636	High Similarity	NPC473126
0.8611	High Similarity	NPC190837
0.8598	High Similarity	NPC306746
0.8598	High Similarity	NPC57362
0.8598	High Similarity	NPC246205
0.8598	High Similarity	NPC265655
0.8598	High Similarity	NPC167383
0.8598	High Similarity	NPC237503
0.8598	High Similarity	NPC204407
0.8585	High Similarity	NPC293512
0.8571	High Similarity	NPC127530
0.8571	High Similarity	NPC279143
0.8571	High Similarity	NPC473920
0.8545	High Similarity	NPC18547
0.8545	High Similarity	NPC74727
0.8545	High Similarity	NPC475633
0.8545	High Similarity	NPC474906
0.8532	High Similarity	NPC174836
0.8532	High Similarity	NPC477253
0.8532	High Similarity	NPC11252
0.8532	High Similarity	NPC289312
0.8532	High Similarity	NPC212968
0.8532	High Similarity	NPC161434
0.8532	High Similarity	NPC64106
0.8532	High Similarity	NPC195132
0.8532	High Similarity	NPC65590
0.8532	High Similarity	NPC125923
0.8529	High Similarity	NPC278506
0.8519	High Similarity	NPC476887
0.8519	High Similarity	NPC90856
0.8519	High Similarity	NPC199457
0.8519	High Similarity	NPC154856
0.8519	High Similarity	NPC7870
0.8519	High Similarity	NPC127056
0.8519	High Similarity	NPC475317
0.8519	High Similarity	NPC279554
0.8519	High Similarity	NPC52241
0.8519	High Similarity	NPC475296
0.8519	High Similarity	NPC476883
0.8519	High Similarity	NPC75747
0.8519	High Similarity	NPC110139
0.8519	High Similarity	NPC270667
0.8519	High Similarity	NPC29069
0.8519	High Similarity	NPC136877
0.8519	High Similarity	NPC274507
0.8519	High Similarity	NPC476885
0.8519	High Similarity	NPC174679
0.8519	High Similarity	NPC68419
0.8519	High Similarity	NPC476882
0.8519	High Similarity	NPC83005
0.8519	High Similarity	NPC476886
0.8519	High Similarity	NPC474589
0.8519	High Similarity	NPC102914
0.8519	High Similarity	NPC56713
0.8519	High Similarity	NPC108709
0.8519	High Similarity	NPC476881
0.8519	High Similarity	NPC59804
0.8519	High Similarity	NPC476880
0.8519	High Similarity	NPC476884
0.8519	High Similarity	NPC164194
0.8509	High Similarity	NPC28532
0.8509	High Similarity	NPC471965
0.8505	High Similarity	NPC94942
0.8505	High Similarity	NPC476123
0.8505	High Similarity	NPC284807
0.8505	High Similarity	NPC195708
0.8505	High Similarity	NPC177246
0.8505	High Similarity	NPC293850
0.8505	High Similarity	NPC28198
0.8496	Intermediate Similarity	NPC48692
0.8491	Intermediate Similarity	NPC210178
0.8468	Intermediate Similarity	NPC134869
0.8468	Intermediate Similarity	NPC152199
0.8468	Intermediate Similarity	NPC302471
0.8468	Intermediate Similarity	NPC235539
0.8462	Intermediate Similarity	NPC245094
0.8455	Intermediate Similarity	NPC255017
0.8455	Intermediate Similarity	NPC75167
0.8455	Intermediate Similarity	NPC311592
0.8455	Intermediate Similarity	NPC251309
0.8455	Intermediate Similarity	NPC471627
0.8455	Intermediate Similarity	NPC471173
0.844	Intermediate Similarity	NPC285410
0.844	Intermediate Similarity	NPC211798
0.844	Intermediate Similarity	NPC164419
0.844	Intermediate Similarity	NPC201992
0.844	Intermediate Similarity	NPC235841
0.844	Intermediate Similarity	NPC292196
0.844	Intermediate Similarity	NPC30397
0.844	Intermediate Similarity	NPC263827
0.844	Intermediate Similarity	NPC108748
0.844	Intermediate Similarity	NPC297208
0.844	Intermediate Similarity	NPC179434
0.844	Intermediate Similarity	NPC473481
0.844	Intermediate Similarity	NPC250481
0.844	Intermediate Similarity	NPC31839
0.844	Intermediate Similarity	NPC191763
0.8435	Intermediate Similarity	NPC14617
0.8435	Intermediate Similarity	NPC262199
0.8435	Intermediate Similarity	NPC202666
0.8435	Intermediate Similarity	NPC471961
0.8435	Intermediate Similarity	NPC471964
0.8426	Intermediate Similarity	NPC118225
0.8426	Intermediate Similarity	NPC477070
0.8426	Intermediate Similarity	NPC477069
0.8426	Intermediate Similarity	NPC127853
0.8421	Intermediate Similarity	NPC275675
0.8416	Intermediate Similarity	NPC305160
0.8411	Intermediate Similarity	NPC473538
0.8411	Intermediate Similarity	NPC283849
0.8407	Intermediate Similarity	NPC190939
0.8407	Intermediate Similarity	NPC197003
0.8393	Intermediate Similarity	NPC477252
0.8381	Intermediate Similarity	NPC223834
0.8378	Intermediate Similarity	NPC116024
0.8378	Intermediate Similarity	NPC472274
0.8378	Intermediate Similarity	NPC165439
0.8378	Intermediate Similarity	NPC477580
0.8378	Intermediate Similarity	NPC220293
0.8378	Intermediate Similarity	NPC181145
0.8364	Intermediate Similarity	NPC80843
0.8364	Intermediate Similarity	NPC256798
0.8364	Intermediate Similarity	NPC109079
0.8364	Intermediate Similarity	NPC139044
0.8364	Intermediate Similarity	NPC10320
0.8364	Intermediate Similarity	NPC471383
0.8364	Intermediate Similarity	NPC130427
0.8364	Intermediate Similarity	NPC101744
0.8364	Intermediate Similarity	NPC1046
0.8364	Intermediate Similarity	NPC233003
0.8364	Intermediate Similarity	NPC48249
0.8364	Intermediate Similarity	NPC475516
0.8364	Intermediate Similarity	NPC116794
0.8364	Intermediate Similarity	NPC102439
0.8364	Intermediate Similarity	NPC79718
0.8364	Intermediate Similarity	NPC139894
0.8364	Intermediate Similarity	NPC104400
0.8364	Intermediate Similarity	NPC475504
0.8364	Intermediate Similarity	NPC324875
0.8364	Intermediate Similarity	NPC37739
0.8364	Intermediate Similarity	NPC104071
0.8364	Intermediate Similarity	NPC292677
0.8364	Intermediate Similarity	NPC210420
0.8364	Intermediate Similarity	NPC276093
0.8364	Intermediate Similarity	NPC469946
0.8364	Intermediate Similarity	NPC257468
0.8364	Intermediate Similarity	NPC473373
0.8364	Intermediate Similarity	NPC473383
0.8364	Intermediate Similarity	NPC46388
0.8364	Intermediate Similarity	NPC128925
0.8364	Intermediate Similarity	NPC474265
0.8362	Intermediate Similarity	NPC471963
0.8362	Intermediate Similarity	NPC247315
0.8362	Intermediate Similarity	NPC471962
0.8349	Intermediate Similarity	NPC470065
0.8349	Intermediate Similarity	NPC242611
0.8348	Intermediate Similarity	NPC275343
0.8333	Intermediate Similarity	NPC285576
0.8333	Intermediate Similarity	NPC241192
0.8319	Intermediate Similarity	NPC239293
0.8319	Intermediate Similarity	NPC297179
0.8319	Intermediate Similarity	NPC286347
0.8319	Intermediate Similarity	NPC234522
0.8318	Intermediate Similarity	NPC475611
0.8318	Intermediate Similarity	NPC162033
0.8304	Intermediate Similarity	NPC31797
0.8291	Intermediate Similarity	NPC47113
0.8291	Intermediate Similarity	NPC285091
0.8291	Intermediate Similarity	NPC174367
0.8288	Intermediate Similarity	NPC475208
0.8288	Intermediate Similarity	NPC150400
0.8288	Intermediate Similarity	NPC151543
0.8288	Intermediate Similarity	NPC473826
0.8288	Intermediate Similarity	NPC155410
0.8288	Intermediate Similarity	NPC124296
0.8288	Intermediate Similarity	NPC73318
0.8288	Intermediate Similarity	NPC475287
0.8288	Intermediate Similarity	NPC96641
0.8288	Intermediate Similarity	NPC51978
0.8288	Intermediate Similarity	NPC166422
0.8288	Intermediate Similarity	NPC320118
0.8288	Intermediate Similarity	NPC114304

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 NPC272576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1787
0.2-0.3	3813
0.3-0.4	2150
0.4-0.5	684
0.5-0.6	263
0.6-0.7	168
0.7-0.8	73
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
0.8598	High Similarity	NPD8132	Clinical (unspecified phase)
0.8585	High Similarity	NPD6412	Phase 2
0.8435	Intermediate Similarity	NPD8328	Phase 3
0.807	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD6370	Approved
0.8	Intermediate Similarity	NPD6686	Approved
0.7983	Intermediate Similarity	NPD7507	Approved
0.7863	Intermediate Similarity	NPD6054	Approved
0.7851	Intermediate Similarity	NPD7736	Approved
0.7787	Intermediate Similarity	NPD7319	Approved
0.7719	Intermediate Similarity	NPD6882	Approved
0.7712	Intermediate Similarity	NPD6059	Approved
0.7647	Intermediate Similarity	NPD6015	Approved
0.7647	Intermediate Similarity	NPD6016	Approved
0.7623	Intermediate Similarity	NPD8293	Discontinued
0.7607	Intermediate Similarity	NPD6009	Approved
0.7603	Intermediate Similarity	NPD7492	Approved
0.7583	Intermediate Similarity	NPD5988	Approved
0.7565	Intermediate Similarity	NPD8297	Approved
0.7563	Intermediate Similarity	NPD6319	Approved
0.7541	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.748	Intermediate Similarity	NPD7078	Approved
0.7395	Intermediate Similarity	NPD7328	Approved
0.7395	Intermediate Similarity	NPD7327	Approved
0.7383	Intermediate Similarity	NPD7748	Approved
0.7377	Intermediate Similarity	NPD6067	Discontinued
0.7368	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6899	Approved
0.7368	Intermediate Similarity	NPD6881	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7358	Intermediate Similarity	NPD6079	Approved
0.7355	Intermediate Similarity	NPD7503	Approved
0.7355	Intermediate Similarity	NPD8515	Approved
0.7355	Intermediate Similarity	NPD8513	Phase 3
0.7355	Intermediate Similarity	NPD8516	Approved
0.7355	Intermediate Similarity	NPD8517	Approved
0.735	Intermediate Similarity	NPD8133	Approved
0.7345	Intermediate Similarity	NPD6675	Approved
0.7345	Intermediate Similarity	NPD6402	Approved
0.7345	Intermediate Similarity	NPD7128	Approved
0.7345	Intermediate Similarity	NPD5739	Approved
0.7339	Intermediate Similarity	NPD7902	Approved
0.7333	Intermediate Similarity	NPD7516	Approved
0.7333	Intermediate Similarity	NPD5328	Approved
0.7328	Intermediate Similarity	NPD6650	Approved
0.7328	Intermediate Similarity	NPD6649	Approved
0.7304	Intermediate Similarity	NPD6373	Approved
0.7304	Intermediate Similarity	NPD6372	Approved
0.7281	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD8294	Approved
0.7273	Intermediate Similarity	NPD8377	Approved
0.7257	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7290	Approved
0.7241	Intermediate Similarity	NPD7102	Approved
0.7241	Intermediate Similarity	NPD4634	Approved
0.7241	Intermediate Similarity	NPD6883	Approved
0.7217	Intermediate Similarity	NPD7320	Approved
0.7213	Intermediate Similarity	NPD8033	Approved
0.7213	Intermediate Similarity	NPD8379	Approved
0.7213	Intermediate Similarity	NPD8380	Approved
0.7213	Intermediate Similarity	NPD8296	Approved
0.7213	Intermediate Similarity	NPD8378	Approved
0.7213	Intermediate Similarity	NPD8335	Approved
0.7207	Intermediate Similarity	NPD5285	Approved
0.7207	Intermediate Similarity	NPD5286	Approved
0.7207	Intermediate Similarity	NPD4696	Approved
0.7196	Intermediate Similarity	NPD6411	Approved
0.7182	Intermediate Similarity	NPD4755	Approved
0.7179	Intermediate Similarity	NPD6869	Approved
0.7179	Intermediate Similarity	NPD6847	Approved
0.7179	Intermediate Similarity	NPD8130	Phase 1
0.7179	Intermediate Similarity	NPD6617	Approved
0.7155	Intermediate Similarity	NPD6012	Approved
0.7155	Intermediate Similarity	NPD6013	Approved
0.7155	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD3573	Approved
0.7143	Intermediate Similarity	NPD6033	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.7097	Intermediate Similarity	NPD7604	Phase 2
0.7091	Intermediate Similarity	NPD5222	Approved
0.7091	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5224	Approved
0.708	Intermediate Similarity	NPD5226	Approved
0.708	Intermediate Similarity	NPD5211	Phase 2
0.708	Intermediate Similarity	NPD5225	Approved
0.708	Intermediate Similarity	NPD4633	Approved
0.7073	Intermediate Similarity	NPD5983	Phase 2
0.7069	Intermediate Similarity	NPD6011	Approved
0.7064	Intermediate Similarity	NPD7900	Approved
0.7064	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4700	Approved
0.7048	Intermediate Similarity	NPD3618	Phase 1
0.7027	Intermediate Similarity	NPD5173	Approved
0.7025	Intermediate Similarity	NPD7115	Discovery
0.7018	Intermediate Similarity	NPD5175	Approved
0.7018	Intermediate Similarity	NPD5174	Approved
0.7009	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6101	Approved
0.6991	Remote Similarity	NPD5223	Approved
0.6984	Remote Similarity	NPD6336	Discontinued
0.6964	Remote Similarity	NPD7638	Approved
0.6957	Remote Similarity	NPD5141	Approved
0.6949	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4697	Phase 3
0.6923	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD4730	Approved
0.6903	Remote Similarity	NPD7640	Approved
0.6903	Remote Similarity	NPD7639	Approved
0.6897	Remote Similarity	NPD6008	Approved
0.6897	Remote Similarity	NPD4767	Approved
0.6897	Remote Similarity	NPD4768	Approved
0.6891	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5779	Approved
0.6818	Remote Similarity	NPD6399	Phase 3
0.6818	Remote Similarity	NPD4202	Approved
0.6807	Remote Similarity	NPD5248	Approved
0.6807	Remote Similarity	NPD5247	Approved
0.6807	Remote Similarity	NPD5251	Approved
0.6807	Remote Similarity	NPD5249	Phase 3
0.6807	Remote Similarity	NPD5250	Approved
0.68	Remote Similarity	NPD6921	Approved
0.6789	Remote Similarity	NPD46	Approved
0.6789	Remote Similarity	NPD6698	Approved
0.6774	Remote Similarity	NPD7101	Approved
0.6774	Remote Similarity	NPD7100	Approved
0.6726	Remote Similarity	NPD6084	Phase 2
0.6726	Remote Similarity	NPD6083	Phase 2
0.6724	Remote Similarity	NPD4754	Approved
0.6698	Remote Similarity	NPD3665	Phase 1
0.6698	Remote Similarity	NPD3133	Approved
0.6698	Remote Similarity	NPD4786	Approved
0.6698	Remote Similarity	NPD3666	Approved
0.6696	Remote Similarity	NPD5695	Phase 3
0.6695	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6335	Approved
0.6694	Remote Similarity	NPD7641	Discontinued
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD6274	Approved
0.6639	Remote Similarity	NPD5128	Approved
0.6613	Remote Similarity	NPD6317	Approved
0.6612	Remote Similarity	NPD5216	Approved
0.6612	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5215	Approved
0.6612	Remote Similarity	NPD5217	Approved
0.6606	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7260	Phase 2
0.6577	Remote Similarity	NPD7983	Approved
0.6574	Remote Similarity	NPD5330	Approved
0.6574	Remote Similarity	NPD5279	Phase 3
0.6574	Remote Similarity	NPD6684	Approved
0.6574	Remote Similarity	NPD7334	Approved
0.6574	Remote Similarity	NPD6409	Approved
0.6574	Remote Similarity	NPD7146	Approved
0.6574	Remote Similarity	NPD7521	Approved
0.656	Remote Similarity	NPD6313	Approved
0.656	Remote Similarity	NPD6314	Approved
0.6545	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4753	Phase 2
0.6538	Remote Similarity	NPD7645	Phase 2
0.6535	Remote Similarity	NPD6909	Approved
0.6535	Remote Similarity	NPD6908	Approved
0.6529	Remote Similarity	NPD5135	Approved
0.6529	Remote Similarity	NPD5169	Approved
0.6529	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4225	Approved
0.6515	Remote Similarity	NPD6914	Discontinued
0.6515	Remote Similarity	NPD5956	Approved
0.65	Remote Similarity	NPD5168	Approved
0.6496	Remote Similarity	NPD7632	Discontinued
0.6475	Remote Similarity	NPD5127	Approved
0.646	Remote Similarity	NPD5282	Discontinued
0.6455	Remote Similarity	NPD5737	Approved
0.6455	Remote Similarity	NPD6903	Approved
0.6455	Remote Similarity	NPD6672	Approved
0.6429	Remote Similarity	NPD8035	Phase 2
0.6429	Remote Similarity	NPD5284	Approved
0.6429	Remote Similarity	NPD8034	Phase 2
0.6429	Remote Similarity	NPD5281	Approved
0.6423	Remote Similarity	NPD6053	Discontinued
0.6422	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD8338	Approved
0.641	Remote Similarity	NPD5344	Discontinued
0.6406	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5210	Approved
0.6404	Remote Similarity	NPD4629	Approved
0.6379	Remote Similarity	NPD5696	Approved
0.6379	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD8171	Discontinued
0.6364	Remote Similarity	NPD8337	Approved
0.6364	Remote Similarity	NPD8336	Approved
0.6357	Remote Similarity	NPD8080	Discontinued
0.6348	Remote Similarity	NPD7614	Phase 1
0.633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.633	Remote Similarity	NPD1694	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