NPASS Compound

Structure

CID195708 OpenBabel06191715582D 46 50 0 0 1 0 0 0 0 0999 V2000 -3.3357 3.3951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7825 2.7035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1342 1.6016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0227 -4.8470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6579 -6.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5396 -5.7103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8074 -2.7087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2543 -1.2355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2544 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5810 0.9101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9803 0.0133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1054 -4.7097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9564 -5.2010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5535 -2.2538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9564 -2.2537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5082 -3.7270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6578 -3.2357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5536 -3.2358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1054 -1.7624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8501 0.4908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7587 2.6009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1580 1.7042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0887 -4.5435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4033 -0.7808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4034 -1.7625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9564 -3.2357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1054 -3.7271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7002 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8074 -4.7097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5082 -4.7096 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7002 -0.9816 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8501 -1.4724 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4271 -0.6783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9816 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6578 -5.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8074 -3.7270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2544 -2.2538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2544 -3.2358 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8844 -3.5828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5503 0.4908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5503 -1.4725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8501 -2.4541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0278 0.2185 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 -8.3588 -5.2007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8501 -1.4724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 2 0 0 0 0 4 23 1 0 0 0 0 5 35 1 0 0 0 0 6 35 1 0 0 0 0 8 37 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 30 1 0 0 0 0 17 36 1 0 0 0 0 18 38 1 0 0 0 0 19 37 1 0 0 0 0 20 28 1 0 0 0 0 20 44 1 0 0 0 0 21 22 1 0 0 0 0 23 39 2 0 0 0 0 23 45 1 0 0 0 0 24 11 1 1 0 0 0 24 25 1 0 0 0 0 24 33 1 0 0 0 0 25 37 1 1 0 0 0 26 27 2 0 0 0 0 26 36 1 0 0 0 0 27 38 1 0 0 0 0 28 31 1 0 0 0 0 28 40 1 1 0 0 0 29 35 1 0 0 0 0 29 36 1 1 0 0 0 30 35 1 0 0 0 0 30 45 1 6 0 0 0 31 32 1 0 0 0 0 31 41 1 6 0 0 0 32 34 1 0 0 0 0 32 42 1 1 0 0 0 33 43 2 0 0 0 0 33 46 1 0 0 0 0 34 44 1 0 0 0 0 34 46 1 6 0 0 0 36 7 1 1 0 0 0 37 38 1 1 0 0 0 38 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.43
Volume:	682.798
LogP:	5.254
LogD:	4.367
LogS:	-5.295
# Rotatable Bonds:	10
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	5.406
Fsp3:	0.842
Lipinski Rule-of-5:	Rejected
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:	-5.038
MDCK Permeability:	1.3577599020209163e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.126

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	91.54781341552734%
Volume Distribution (VD):	1.449
Pgp-substrate:	2.915351390838623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.505
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.433
CYP3A4-inhibitor:	0.259
CYP3A4-substrate:	0.507

ADMET: Excretion

Clearance (CL):	2.357
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.502
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.479
Skin Sensitization:	0.16
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC195708

Natural Product ID:	NPC195708
*Common Name:**	Fomitoside G
IUPAC Name:	[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl] (2R)-2-[(3R,5R,10S,13R,14R,17R)-3-acetyloxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoate
Synonyms:	Fomitoside G
Standard InCHIKey:	XLFNYXBDIFFFJX-PAMRNPGQSA-N
Standard InCHI:	InChI=1S/C38H60O8/c1-21(2)22(3)10-11-24(33(43)46-34-32(42)31(41)28(40)20-44-34)25-14-18-38(9)27-12-13-29-35(5,6)30(45-23(4)39)16-17-36(29,7)26(27)15-19-37(25,38)8/h21,24-25,28-32,34,40-42H,3,10-20H2,1-2,4-9H3/t24-,25-,28-,29+,30-,31+,32-,34+,36-,37-,38+/m1/s1
SMILES:	CC(C)C(=C)CC[C@H]([C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](C(C)(C)[C@@H]1CC3)OC(=O)C)C(=O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508658
PubChem CID:	11399538
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15679320]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	fruit bodies	Tokushima, Japan	1999-Autumn	PMID[15679320]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	21.7	%	PMID[491536]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	INH	=	1.85	10'-5M	PMID[491536]

☑ 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 NPC195708 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	215
0.1-0.2	1387
0.2-0.3	4884
0.3-0.4	11644
0.4-0.5	9764
0.5-0.6	5733
0.6-0.7	5205
0.7-0.8	3311
0.8-0.85	481
0.85-0.9	48
0.9-0.95	15
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC265655
0.9802	High Similarity	NPC129340
0.9706	High Similarity	NPC292196
0.9612	High Similarity	NPC233003
0.9519	High Similarity	NPC251309
0.9515	High Similarity	NPC263827
0.9515	High Similarity	NPC250481
0.9515	High Similarity	NPC285410
0.951	High Similarity	NPC477069
0.951	High Similarity	NPC477070
0.95	High Similarity	NPC223741
0.9429	High Similarity	NPC220293
0.9429	High Similarity	NPC116024
0.9406	High Similarity	NPC162033
0.9327	High Similarity	NPC477073
0.9231	High Similarity	NPC114961
0.9231	High Similarity	NPC27551
0.9223	High Similarity	NPC295389
0.9159	High Similarity	NPC244127
0.9151	High Similarity	NPC477074
0.9135	High Similarity	NPC137917
0.9065	High Similarity	NPC473882
0.9048	High Similarity	NPC101450
0.9048	High Similarity	NPC78046
0.9048	High Similarity	NPC52241
0.9048	High Similarity	NPC269095
0.9048	High Similarity	NPC475317
0.9048	High Similarity	NPC220984
0.9048	High Similarity	NPC154856
0.9038	High Similarity	NPC28198
0.9038	High Similarity	NPC88744
0.9038	High Similarity	NPC476123
0.9038	High Similarity	NPC284807
0.9038	High Similarity	NPC177246
0.8972	High Similarity	NPC200944
0.8972	High Similarity	NPC73455
0.8972	High Similarity	NPC260665
0.8962	High Similarity	NPC269466
0.8952	High Similarity	NPC473844
0.8952	High Similarity	NPC167383
0.8952	High Similarity	NPC204407
0.8952	High Similarity	NPC57362
0.8952	High Similarity	NPC306746
0.8952	High Similarity	NPC127853
0.8952	High Similarity	NPC118225
0.8952	High Similarity	NPC240125
0.8952	High Similarity	NPC51947
0.8952	High Similarity	NPC91583
0.8952	High Similarity	NPC237503
0.8942	High Similarity	NPC283849
0.8942	High Similarity	NPC293512
0.8942	High Similarity	NPC473538
0.8922	High Similarity	NPC94919
0.8919	High Similarity	NPC202051
0.8879	High Similarity	NPC210420
0.8879	High Similarity	NPC130427
0.8879	High Similarity	NPC477253
0.8879	High Similarity	NPC474265
0.8868	High Similarity	NPC199457
0.8868	High Similarity	NPC476885
0.8868	High Similarity	NPC476884
0.8868	High Similarity	NPC59804
0.8868	High Similarity	NPC68419
0.8868	High Similarity	NPC279554
0.8868	High Similarity	NPC90856
0.8868	High Similarity	NPC75747
0.8868	High Similarity	NPC474589
0.8868	High Similarity	NPC476887
0.8868	High Similarity	NPC56713
0.8868	High Similarity	NPC127056
0.8868	High Similarity	NPC110139
0.8868	High Similarity	NPC475296
0.8868	High Similarity	NPC274507
0.8868	High Similarity	NPC108709
0.8868	High Similarity	NPC476883
0.8868	High Similarity	NPC136877
0.8868	High Similarity	NPC270667
0.8868	High Similarity	NPC476882
0.8868	High Similarity	NPC29069
0.8868	High Similarity	NPC476886
0.8868	High Similarity	NPC164194
0.8868	High Similarity	NPC476881
0.8868	High Similarity	NPC174679
0.8868	High Similarity	NPC476880
0.8868	High Similarity	NPC242611
0.8868	High Similarity	NPC7870
0.8868	High Similarity	NPC102914
0.8846	High Similarity	NPC473199
0.8846	High Similarity	NPC475611
0.8829	High Similarity	NPC471406
0.8818	High Similarity	NPC239293
0.8785	High Similarity	NPC91838
0.8785	High Similarity	NPC30397
0.8785	High Similarity	NPC11035
0.8785	High Similarity	NPC297208
0.8785	High Similarity	NPC164419
0.8785	High Similarity	NPC108748
0.8785	High Similarity	NPC235841
0.8785	High Similarity	NPC179434
0.8785	High Similarity	NPC272242
0.8785	High Similarity	NPC240734
0.8785	High Similarity	NPC211798
0.8785	High Similarity	NPC1876
0.8785	High Similarity	NPC191763
0.8785	High Similarity	NPC190837
0.8785	High Similarity	NPC275668
0.8785	High Similarity	NPC204392
0.8785	High Similarity	NPC473481
0.8785	High Similarity	NPC31839
0.8774	High Similarity	NPC475364
0.8762	High Similarity	NPC234160
0.8739	High Similarity	NPC477071
0.8716	High Similarity	NPC474557
0.8716	High Similarity	NPC74727
0.8704	High Similarity	NPC469946
0.8704	High Similarity	NPC471967
0.8704	High Similarity	NPC125923
0.8704	High Similarity	NPC104400
0.8704	High Similarity	NPC243572
0.8704	High Similarity	NPC473383
0.8704	High Similarity	NPC276093
0.8704	High Similarity	NPC65590
0.8704	High Similarity	NPC46388
0.8704	High Similarity	NPC257468
0.8704	High Similarity	NPC100383
0.8704	High Similarity	NPC101744
0.8704	High Similarity	NPC471383
0.8704	High Similarity	NPC212968
0.8704	High Similarity	NPC473373
0.8704	High Similarity	NPC37739
0.8704	High Similarity	NPC475504
0.8704	High Similarity	NPC470543
0.8704	High Similarity	NPC475516
0.8704	High Similarity	NPC102439
0.8704	High Similarity	NPC104071
0.8704	High Similarity	NPC128925
0.8704	High Similarity	NPC161434
0.8704	High Similarity	NPC109079
0.8704	High Similarity	NPC48249
0.8704	High Similarity	NPC10320
0.8704	High Similarity	NPC79718
0.8704	High Similarity	NPC80843
0.8704	High Similarity	NPC1046
0.8704	High Similarity	NPC292677
0.8704	High Similarity	NPC256798
0.8704	High Similarity	NPC116794
0.8704	High Similarity	NPC139894
0.8704	High Similarity	NPC139044
0.8704	High Similarity	NPC324875
0.8704	High Similarity	NPC195132
0.8704	High Similarity	NPC64106
0.8692	High Similarity	NPC90630
0.8692	High Similarity	NPC475243
0.8684	High Similarity	NPC130229
0.8679	High Similarity	NPC472988
0.8679	High Similarity	NPC258323
0.8679	High Similarity	NPC38217
0.8679	High Similarity	NPC285576
0.8667	High Similarity	NPC210178
0.8661	High Similarity	NPC470312
0.8649	High Similarity	NPC291564
0.8641	High Similarity	NPC21064
0.8641	High Similarity	NPC121072
0.8636	High Similarity	NPC279638
0.8624	High Similarity	NPC475467
0.8624	High Similarity	NPC473343
0.8624	High Similarity	NPC138334
0.8624	High Similarity	NPC189884
0.8624	High Similarity	NPC241909
0.8624	High Similarity	NPC295823
0.8624	High Similarity	NPC114304
0.8624	High Similarity	NPC46665
0.8624	High Similarity	NPC258885
0.8624	High Similarity	NPC133818
0.8624	High Similarity	NPC124296
0.8624	High Similarity	NPC73986
0.8624	High Similarity	NPC192600
0.8624	High Similarity	NPC47063
0.8624	High Similarity	NPC251263
0.8624	High Similarity	NPC174720
0.8624	High Similarity	NPC323341
0.8624	High Similarity	NPC134835
0.8624	High Similarity	NPC166422
0.8624	High Similarity	NPC475208
0.8624	High Similarity	NPC150400
0.8624	High Similarity	NPC204458
0.8624	High Similarity	NPC146563
0.8624	High Similarity	NPC155410
0.8624	High Similarity	NPC114287
0.8624	High Similarity	NPC163183
0.8624	High Similarity	NPC238935
0.8624	High Similarity	NPC102619
0.8624	High Similarity	NPC151543
0.8624	High Similarity	NPC269315
0.8624	High Similarity	NPC473826
0.8624	High Similarity	NPC219180
0.8624	High Similarity	NPC73318
0.8624	High Similarity	NPC271138
0.8624	High Similarity	NPC309714
0.8624	High Similarity	NPC96641

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 NPC195708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1731
0.2-0.3	4025
0.3-0.4	2094
0.4-0.5	594
0.5-0.6	244
0.6-0.7	187
0.7-0.8	95
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8774	High Similarity	NPD8132	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD6412	Phase 2
0.8288	Intermediate Similarity	NPD8133	Approved
0.8136	Intermediate Similarity	NPD7507	Approved
0.807	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6686	Approved
0.7966	Intermediate Similarity	NPD8328	Phase 3
0.7934	Intermediate Similarity	NPD7319	Approved
0.7863	Intermediate Similarity	NPD8377	Approved
0.7863	Intermediate Similarity	NPD8294	Approved
0.7851	Intermediate Similarity	NPD7736	Approved
0.7845	Intermediate Similarity	NPD7328	Approved
0.7845	Intermediate Similarity	NPD7327	Approved
0.7797	Intermediate Similarity	NPD8033	Approved
0.7797	Intermediate Similarity	NPD8380	Approved
0.7797	Intermediate Similarity	NPD8296	Approved
0.7797	Intermediate Similarity	NPD8378	Approved
0.7797	Intermediate Similarity	NPD8379	Approved
0.7797	Intermediate Similarity	NPD8335	Approved
0.7778	Intermediate Similarity	NPD7516	Approved
0.7769	Intermediate Similarity	NPD8293	Discontinued
0.7719	Intermediate Similarity	NPD6882	Approved
0.7719	Intermediate Similarity	NPD8297	Approved
0.7692	Intermediate Similarity	NPD8034	Phase 2
0.7692	Intermediate Similarity	NPD8035	Phase 2
0.7647	Intermediate Similarity	NPD7503	Approved
0.7619	Intermediate Similarity	NPD6399	Phase 3
0.7583	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.7459	Intermediate Similarity	NPD7492	Approved
0.7458	Intermediate Similarity	NPD6009	Approved
0.7456	Intermediate Similarity	NPD6373	Approved
0.7456	Intermediate Similarity	NPD6372	Approved
0.7451	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6319	Approved
0.7417	Intermediate Similarity	NPD6059	Approved
0.7417	Intermediate Similarity	NPD6054	Approved
0.7411	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6616	Approved
0.7383	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD7320	Approved
0.7368	Intermediate Similarity	NPD6899	Approved
0.7368	Intermediate Similarity	NPD6881	Approved
0.7355	Intermediate Similarity	NPD8516	Approved
0.7355	Intermediate Similarity	NPD8515	Approved
0.7355	Intermediate Similarity	NPD8513	Phase 3
0.7355	Intermediate Similarity	NPD8517	Approved
0.735	Intermediate Similarity	NPD4632	Approved
0.7339	Intermediate Similarity	NPD7078	Approved
0.7339	Intermediate Similarity	NPD7902	Approved
0.7328	Intermediate Similarity	NPD8130	Phase 1
0.7328	Intermediate Similarity	NPD6650	Approved
0.7328	Intermediate Similarity	NPD6649	Approved
0.7311	Intermediate Similarity	NPD7115	Discovery
0.7281	Intermediate Similarity	NPD5697	Approved
0.7281	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD7638	Approved
0.7241	Intermediate Similarity	NPD7290	Approved
0.7241	Intermediate Similarity	NPD7102	Approved
0.7241	Intermediate Similarity	NPD6883	Approved
0.7236	Intermediate Similarity	NPD6067	Discontinued
0.7213	Intermediate Similarity	NPD6016	Approved
0.7213	Intermediate Similarity	NPD6015	Approved
0.7207	Intermediate Similarity	NPD7640	Approved
0.7207	Intermediate Similarity	NPD7639	Approved
0.7196	Intermediate Similarity	NPD7515	Phase 2
0.7184	Intermediate Similarity	NPD4786	Approved
0.7182	Intermediate Similarity	NPD6083	Phase 2
0.7182	Intermediate Similarity	NPD6084	Phase 2
0.7179	Intermediate Similarity	NPD6869	Approved
0.7179	Intermediate Similarity	NPD6847	Approved
0.7179	Intermediate Similarity	NPD6617	Approved
0.717	Intermediate Similarity	NPD5328	Approved
0.7156	Intermediate Similarity	NPD5695	Phase 3
0.7155	Intermediate Similarity	NPD6013	Approved
0.7155	Intermediate Similarity	NPD6012	Approved
0.7155	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6014	Approved
0.7154	Intermediate Similarity	NPD5988	Approved
0.7069	Intermediate Similarity	NPD6011	Approved
0.7064	Intermediate Similarity	NPD7900	Approved
0.7064	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3618	Phase 1
0.7037	Intermediate Similarity	NPD6411	Approved
0.7037	Intermediate Similarity	NPD6079	Approved
0.7034	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4755	Approved
0.699	Remote Similarity	NPD3667	Approved
0.6972	Remote Similarity	NPD8171	Discontinued
0.6972	Remote Similarity	NPD4202	Approved
0.696	Remote Similarity	NPD7604	Phase 2
0.6949	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5983	Phase 2
0.6916	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5737	Approved
0.6916	Remote Similarity	NPD6672	Approved
0.6903	Remote Similarity	NPD5285	Approved
0.6903	Remote Similarity	NPD4696	Approved
0.6903	Remote Similarity	NPD5286	Approved
0.6903	Remote Similarity	NPD4700	Approved
0.6897	Remote Similarity	NPD6008	Approved
0.6891	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6684	Approved
0.6887	Remote Similarity	NPD7521	Approved
0.6887	Remote Similarity	NPD5330	Approved
0.6887	Remote Similarity	NPD7146	Approved
0.6887	Remote Similarity	NPD6409	Approved
0.6887	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD6033	Approved
0.6852	Remote Similarity	NPD6101	Approved
0.6852	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6336	Discontinued
0.6832	Remote Similarity	NPD6116	Phase 1
0.6814	Remote Similarity	NPD5696	Approved
0.6807	Remote Similarity	NPD4634	Approved
0.6803	Remote Similarity	NPD6274	Approved
0.6803	Remote Similarity	NPD6940	Discontinued
0.6796	Remote Similarity	NPD7525	Registered
0.6786	Remote Similarity	NPD5222	Approved
0.6786	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5221	Approved
0.6786	Remote Similarity	NPD4697	Phase 3
0.6783	Remote Similarity	NPD5224	Approved
0.6783	Remote Similarity	NPD5226	Approved
0.6783	Remote Similarity	NPD7632	Discontinued
0.6783	Remote Similarity	NPD4633	Approved
0.6783	Remote Similarity	NPD5225	Approved
0.6783	Remote Similarity	NPD5211	Phase 2
0.678	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7101	Approved
0.6774	Remote Similarity	NPD7100	Approved
0.6765	Remote Similarity	NPD6115	Approved
0.6765	Remote Similarity	NPD6118	Approved
0.6765	Remote Similarity	NPD6697	Approved
0.6765	Remote Similarity	NPD6114	Approved
0.6759	Remote Similarity	NPD6903	Approved
0.6752	Remote Similarity	NPD4768	Approved
0.6752	Remote Similarity	NPD4767	Approved
0.6733	Remote Similarity	NPD6117	Approved
0.6729	Remote Similarity	NPD5279	Phase 3
0.6727	Remote Similarity	NPD5284	Approved
0.6727	Remote Similarity	NPD5281	Approved
0.6726	Remote Similarity	NPD5173	Approved
0.6724	Remote Similarity	NPD5175	Approved
0.6724	Remote Similarity	NPD5174	Approved
0.6698	Remote Similarity	NPD3665	Phase 1
0.6698	Remote Similarity	NPD3133	Approved
0.6698	Remote Similarity	NPD3666	Approved
0.6697	Remote Similarity	NPD4753	Phase 2
0.6696	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5223	Approved
0.6695	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6639	Remote Similarity	NPD4729	Approved
0.6639	Remote Similarity	NPD4730	Approved
0.6636	Remote Similarity	NPD6698	Approved
0.6636	Remote Similarity	NPD46	Approved
0.6615	Remote Similarity	NPD8337	Approved
0.6615	Remote Similarity	NPD8336	Approved
0.6613	Remote Similarity	NPD6317	Approved
0.6581	Remote Similarity	NPD4754	Approved
0.6577	Remote Similarity	NPD6050	Approved
0.6574	Remote Similarity	NPD6098	Approved
0.656	Remote Similarity	NPD6313	Approved
0.656	Remote Similarity	NPD6314	Approved
0.6557	Remote Similarity	NPD6053	Discontinued
0.6545	Remote Similarity	NPD6673	Approved
0.6545	Remote Similarity	NPD6080	Approved
0.6545	Remote Similarity	NPD6904	Approved
0.6542	Remote Similarity	NPD3668	Phase 3
0.6541	Remote Similarity	NPD8338	Approved
0.6541	Remote Similarity	NPD8449	Approved
0.6538	Remote Similarity	NPD7645	Phase 2
0.6535	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5247	Approved
0.6529	Remote Similarity	NPD5249	Phase 3
0.6529	Remote Similarity	NPD5248	Approved
0.6529	Remote Similarity	NPD5250	Approved
0.6529	Remote Similarity	NPD5251	Approved
0.6518	Remote Similarity	NPD5778	Approved
0.6518	Remote Similarity	NPD5779	Approved
0.6514	Remote Similarity	NPD3573	Approved
0.65	Remote Similarity	NPD5128	Approved
0.6493	Remote Similarity	NPD8450	Suspended
0.6486	Remote Similarity	NPD5692	Phase 3
0.6471	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD6942	Approved
0.6449	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3669	Approved
0.6434	Remote Similarity	NPD7122	Discontinued
0.6429	Remote Similarity	NPD5694	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