NPASS Compound

Structure

NPC91583 OpenBabel07101718192D 46 51 0 0 1 0 0 0 0 0999 V2000 -1.5495 -4.5825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2871 -3.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0385 2.3205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0577 2.3205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8494 0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 -1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8781 -3.0234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2770 -2.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5481 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 -0.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2037 0.6017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2464 -3.6497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9027 -2.9209 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8494 -1.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8494 1.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3975 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2284 0.7042 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8494 -0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6987 -1.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8294 1.6002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8540 1.7027 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2776 0.9092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6987 0.9808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3975 0.9808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6765 0.0132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1246 -0.6777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 1.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6987 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8494 -0.4904 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5481 -1.4712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7802 1.3951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8494 2.4519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2469 -0.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4059 2.3936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4551 2.5987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3022 1.0117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2469 1.4712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7257 0.2183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6519 -0.0893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1000 -0.7802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 6 34 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 36 1 0 0 0 0 12 13 1 0 0 0 0 12 34 1 0 0 0 0 13 36 1 0 0 0 0 14 21 1 0 0 0 0 14 33 1 0 0 0 0 15 20 1 0 0 0 0 15 35 1 0 0 0 0 16 37 1 0 0 0 0 18 17 1 6 0 0 0 18 24 1 0 0 0 0 19 24 1 0 0 0 0 19 34 1 6 0 0 0 20 28 1 0 0 0 0 20 38 1 1 0 0 0 21 29 1 0 0 0 0 21 39 1 6 0 0 0 22 16 1 6 0 0 0 22 25 1 0 0 0 0 22 45 1 0 0 0 0 23 33 1 1 0 0 0 23 35 1 0 0 0 0 24 36 1 1 0 0 0 25 26 1 0 0 0 0 25 40 1 1 0 0 0 26 27 1 0 0 0 0 26 41 1 6 0 0 0 27 30 1 0 0 0 0 27 42 1 1 0 0 0 28 32 1 0 0 0 0 28 33 1 1 0 0 0 29 32 1 0 0 0 0 29 43 1 1 0 0 0 30 45 1 0 0 0 0 30 46 1 6 0 0 0 31 44 2 0 0 0 0 31 46 1 0 0 0 0 33 5 1 1 0 0 0 34 35 1 1 0 0 0 35 7 1 1 0 0 0 36 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	650.4
Volume:	662.503
LogP:	2.894
LogD:	3.166
LogS:	-3.153
# Rotatable Bonds:	5
TPSA:	177.14
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	5.588
Fsp3:	0.917
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:	-5.482
MDCK Permeability:	2.8919494070578367e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.2
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	79.5453109741211%
Volume Distribution (VD):	0.459
Pgp-substrate:	6.940135478973389%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.56
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.178
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.136
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	1.091
Half-life (T1/2):	0.398

ADMET: Toxicity

hERG Blockers:	0.237
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.076
Skin Sensitization:	0.246
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC91583

Natural Product ID:	NPC91583
*Common Name:**	Quadranoside I
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,3aS,5aR,5bR,7R,7aR,9R,10R,11aR,11bR,13aR,13bR)-7,9,10-trihydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
Synonyms:	Quadranoside I
Standard InCHIKey:	YFVXYEDHMANDIJ-UOLGNBMWSA-N
Standard InCHI:	InChI=1S/C36H58O10/c1-17(2)18-10-11-36(31(44)46-30-27(42)26(41)25(40)22(16-37)45-30)13-12-34(6)19(24(18)36)8-9-23-33(5)14-21(39)29(43)32(3,4)28(33)20(38)15-35(23,34)7/h18-30,37-43H,1,8-16H2,2-7H3/t18-,19+,20+,21+,22+,23+,24+,25+,26-,27+,28-,29-,30-,33+,34+,35+,36-/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@H]3[C@@H]3[C@](CC2)(C)[C@]2(C)C[C@@H](O)[C@@H]4[C@]([C@H]2CC3)(C)C[C@H]([C@@H](C4(C)C)O)O)C(=C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510768
PubChem CID:	10416826
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	6.3	%	PMID[457098]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	37.6	%	PMID[457098]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	29.7	%	PMID[457098]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	71.2	%	PMID[457098]

☑ 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 NPC91583 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	278
0.1-0.2	2068
0.2-0.3	6324
0.3-0.4	13253
0.4-0.5	8309
0.5-0.6	5368
0.6-0.7	3735
0.7-0.8	2081
0.8-0.85	726
0.85-0.9	479
0.9-0.95	58
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC240125
0.99	High Similarity	NPC88744
0.9802	High Similarity	NPC51947
0.9802	High Similarity	NPC473844
0.9612	High Similarity	NPC275668
0.9612	High Similarity	NPC11035
0.9612	High Similarity	NPC240734
0.9612	High Similarity	NPC91838
0.9612	High Similarity	NPC204392
0.9612	High Similarity	NPC1876
0.9429	High Similarity	NPC146563
0.94	High Similarity	NPC94919
0.934	High Similarity	NPC469821
0.9333	High Similarity	NPC470543
0.9252	High Similarity	NPC469820
0.9252	High Similarity	NPC469823
0.9252	High Similarity	NPC137414
0.9238	High Similarity	NPC263827
0.9238	High Similarity	NPC250481
0.9238	High Similarity	NPC285410
0.9238	High Similarity	NPC272242
0.9223	High Similarity	NPC287269
0.9159	High Similarity	NPC54395
0.9151	High Similarity	NPC472719
0.9151	High Similarity	NPC207845
0.9151	High Similarity	NPC243572
0.9143	High Similarity	NPC110139
0.9143	High Similarity	NPC7870
0.9143	High Similarity	NPC75747
0.9143	High Similarity	NPC68419
0.9143	High Similarity	NPC199457
0.9143	High Similarity	NPC102914
0.9143	High Similarity	NPC108709
0.9083	High Similarity	NPC469822
0.9065	High Similarity	NPC102619
0.9065	High Similarity	NPC73986
0.9057	High Similarity	NPC274833
0.9057	High Similarity	NPC179434
0.9048	High Similarity	NPC306746
0.9048	High Similarity	NPC8431
0.9048	High Similarity	NPC167383
0.9048	High Similarity	NPC204407
0.9048	High Similarity	NPC57362
0.9048	High Similarity	NPC127853
0.9048	High Similarity	NPC237503
0.8991	High Similarity	NPC156651
0.8972	High Similarity	NPC233003
0.8972	High Similarity	NPC116794
0.8972	High Similarity	NPC473383
0.8972	High Similarity	NPC139894
0.8972	High Similarity	NPC48249
0.8972	High Similarity	NPC477253
0.8962	High Similarity	NPC174679
0.8962	High Similarity	NPC164194
0.8962	High Similarity	NPC279554
0.8962	High Similarity	NPC476880
0.8962	High Similarity	NPC90856
0.8962	High Similarity	NPC476887
0.8962	High Similarity	NPC59804
0.8962	High Similarity	NPC270667
0.8962	High Similarity	NPC476884
0.8962	High Similarity	NPC474589
0.8962	High Similarity	NPC127056
0.8962	High Similarity	NPC136877
0.8962	High Similarity	NPC475296
0.8962	High Similarity	NPC129340
0.8962	High Similarity	NPC476883
0.8962	High Similarity	NPC476881
0.8962	High Similarity	NPC274507
0.8962	High Similarity	NPC56713
0.8962	High Similarity	NPC29069
0.8962	High Similarity	NPC476882
0.8962	High Similarity	NPC476885
0.8962	High Similarity	NPC220984
0.8962	High Similarity	NPC476886
0.8952	High Similarity	NPC177246
0.8952	High Similarity	NPC476123
0.8952	High Similarity	NPC224414
0.8952	High Similarity	NPC28198
0.8952	High Similarity	NPC284807
0.8952	High Similarity	NPC285576
0.8952	High Similarity	NPC195708
0.8899	High Similarity	NPC244127
0.8899	High Similarity	NPC472718
0.8889	High Similarity	NPC269315
0.8889	High Similarity	NPC163183
0.8889	High Similarity	NPC271138
0.8889	High Similarity	NPC475208
0.8889	High Similarity	NPC150400
0.8889	High Similarity	NPC73318
0.8889	High Similarity	NPC238935
0.8889	High Similarity	NPC473343
0.8889	High Similarity	NPC96641
0.8889	High Similarity	NPC134835
0.8889	High Similarity	NPC251309
0.8879	High Similarity	NPC191763
0.8879	High Similarity	NPC473481
0.8879	High Similarity	NPC31839
0.8879	High Similarity	NPC108748
0.8879	High Similarity	NPC235841
0.8879	High Similarity	NPC297208
0.8879	High Similarity	NPC164419
0.8879	High Similarity	NPC30397
0.8879	High Similarity	NPC211798
0.8868	High Similarity	NPC265655
0.8868	High Similarity	NPC154085
0.8868	High Similarity	NPC125361
0.8868	High Similarity	NPC43976
0.8868	High Similarity	NPC137917
0.8868	High Similarity	NPC296761
0.8868	High Similarity	NPC51925
0.8857	High Similarity	NPC234160
0.8857	High Similarity	NPC283849
0.8857	High Similarity	NPC473538
0.8839	High Similarity	NPC470478
0.8824	High Similarity	NPC317019
0.8807	High Similarity	NPC475633
0.8807	High Similarity	NPC473882
0.8796	High Similarity	NPC80843
0.8796	High Similarity	NPC109079
0.8796	High Similarity	NPC79718
0.8796	High Similarity	NPC256798
0.8796	High Similarity	NPC475504
0.8796	High Similarity	NPC324875
0.8796	High Similarity	NPC139044
0.8796	High Similarity	NPC104071
0.8796	High Similarity	NPC37739
0.8796	High Similarity	NPC475516
0.8796	High Similarity	NPC10320
0.8796	High Similarity	NPC292677
0.8796	High Similarity	NPC471967
0.8796	High Similarity	NPC104400
0.8796	High Similarity	NPC469946
0.8796	High Similarity	NPC276093
0.8796	High Similarity	NPC1046
0.8796	High Similarity	NPC257468
0.8796	High Similarity	NPC101744
0.8796	High Similarity	NPC473373
0.8796	High Similarity	NPC471383
0.8796	High Similarity	NPC46388
0.8796	High Similarity	NPC102439
0.8796	High Similarity	NPC128925
0.8785	High Similarity	NPC269095
0.8785	High Similarity	NPC106760
0.8785	High Similarity	NPC78046
0.8785	High Similarity	NPC242611
0.8774	High Similarity	NPC230888
0.8774	High Similarity	NPC295389
0.8774	High Similarity	NPC472988
0.8774	High Similarity	NPC38217
0.8762	High Similarity	NPC473199
0.8762	High Similarity	NPC475611
0.8762	High Similarity	NPC165405
0.8739	High Similarity	NPC239293
0.8739	High Similarity	NPC475899
0.8725	High Similarity	NPC157739
0.8716	High Similarity	NPC46665
0.8716	High Similarity	NPC174720
0.8716	High Similarity	NPC251263
0.8716	High Similarity	NPC473826
0.8716	High Similarity	NPC47063
0.8716	High Similarity	NPC114287
0.8716	High Similarity	NPC151543
0.8716	High Similarity	NPC309714
0.8716	High Similarity	NPC138334
0.8716	High Similarity	NPC166422
0.8716	High Similarity	NPC219180
0.8716	High Similarity	NPC258885
0.8716	High Similarity	NPC133818
0.8716	High Similarity	NPC189884
0.8716	High Similarity	NPC323341
0.8716	High Similarity	NPC475287
0.8716	High Similarity	NPC192600
0.8716	High Similarity	NPC475467
0.8716	High Similarity	NPC295823
0.8716	High Similarity	NPC155410
0.8716	High Similarity	NPC124296
0.8716	High Similarity	NPC114304
0.8716	High Similarity	NPC241909
0.8716	High Similarity	NPC204458
0.8713	High Similarity	NPC472989
0.8704	High Similarity	NPC65167
0.8704	High Similarity	NPC292196
0.8704	High Similarity	NPC477073
0.87	High Similarity	NPC277399
0.8692	High Similarity	NPC477069
0.8692	High Similarity	NPC477070
0.8667	High Similarity	NPC469827
0.8661	High Similarity	NPC477464
0.8649	High Similarity	NPC471547
0.8649	High Similarity	NPC473405
0.8649	High Similarity	NPC477252
0.8649	High Similarity	NPC473304
0.8649	High Similarity	NPC300419
0.8636	High Similarity	NPC475486
0.8636	High Similarity	NPC236638
0.8636	High Similarity	NPC79643
0.8636	High Similarity	NPC475160
0.8636	High Similarity	NPC294453
0.8636	High Similarity	NPC475140

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 NPC91583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	2447
0.2-0.3	3980
0.3-0.4	1562
0.4-0.5	430
0.5-0.6	282
0.6-0.7	135
0.7-0.8	26
0.8-0.85	14
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD8133	Approved
0.8519	High Similarity	NPD8132	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD8034	Phase 2
0.8137	Intermediate Similarity	NPD8035	Phase 2
0.8067	Intermediate Similarity	NPD7507	Approved
0.8051	Intermediate Similarity	NPD8328	Phase 3
0.8	Intermediate Similarity	NPD6412	Phase 2
0.7982	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD8377	Approved
0.7949	Intermediate Similarity	NPD8294	Approved
0.79	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD8335	Approved
0.7881	Intermediate Similarity	NPD8378	Approved
0.7881	Intermediate Similarity	NPD8380	Approved
0.7881	Intermediate Similarity	NPD8296	Approved
0.7881	Intermediate Similarity	NPD8379	Approved
0.7881	Intermediate Similarity	NPD8033	Approved
0.7869	Intermediate Similarity	NPD7319	Approved
0.7863	Intermediate Similarity	NPD7516	Approved
0.7778	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD7327	Approved
0.7768	Intermediate Similarity	NPD6686	Approved
0.7642	Intermediate Similarity	NPD7736	Approved
0.7547	Intermediate Similarity	NPD8171	Discontinued
0.7438	Intermediate Similarity	NPD7503	Approved
0.7419	Intermediate Similarity	NPD8293	Discontinued
0.7315	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD7902	Approved
0.7236	Intermediate Similarity	NPD6370	Approved
0.7207	Intermediate Similarity	NPD7638	Approved
0.7203	Intermediate Similarity	NPD6882	Approved
0.7203	Intermediate Similarity	NPD8297	Approved
0.72	Intermediate Similarity	NPD6114	Approved
0.72	Intermediate Similarity	NPD6115	Approved
0.72	Intermediate Similarity	NPD6118	Approved
0.72	Intermediate Similarity	NPD6697	Approved
0.7167	Intermediate Similarity	NPD6940	Discontinued
0.7155	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.713	Intermediate Similarity	NPD7515	Phase 2
0.712	Intermediate Similarity	NPD7492	Approved
0.7107	Intermediate Similarity	NPD6009	Approved
0.71	Intermediate Similarity	NPD6116	Phase 1
0.7073	Intermediate Similarity	NPD6059	Approved
0.7073	Intermediate Similarity	NPD6319	Approved
0.7073	Intermediate Similarity	NPD6054	Approved
0.7064	Intermediate Similarity	NPD6399	Phase 3
0.7063	Intermediate Similarity	NPD6616	Approved
0.7016	Intermediate Similarity	NPD8517	Approved
0.7016	Intermediate Similarity	NPD8513	Phase 3
0.7016	Intermediate Similarity	NPD8516	Approved
0.7016	Intermediate Similarity	NPD8515	Approved
0.7008	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD7900	Approved
0.7	Intermediate Similarity	NPD6117	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7128	Approved
0.6983	Remote Similarity	NPD6675	Approved
0.6983	Remote Similarity	NPD5739	Approved
0.6983	Remote Similarity	NPD6402	Approved
0.6949	Remote Similarity	NPD6372	Approved
0.6949	Remote Similarity	NPD6373	Approved
0.6949	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6067	Discontinued
0.688	Remote Similarity	NPD6016	Approved
0.688	Remote Similarity	NPD6015	Approved
0.6864	Remote Similarity	NPD6899	Approved
0.6864	Remote Similarity	NPD6881	Approved
0.6864	Remote Similarity	NPD7320	Approved
0.6833	Remote Similarity	NPD8130	Phase 1
0.6833	Remote Similarity	NPD6650	Approved
0.6833	Remote Similarity	NPD6649	Approved
0.6829	Remote Similarity	NPD7115	Discovery
0.6825	Remote Similarity	NPD5988	Approved
0.68	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5701	Approved
0.678	Remote Similarity	NPD5697	Approved
0.675	Remote Similarity	NPD6883	Approved
0.675	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7102	Approved
0.675	Remote Similarity	NPD7290	Approved
0.6731	Remote Similarity	NPD6928	Phase 2
0.6724	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD6847	Approved
0.6694	Remote Similarity	NPD6617	Approved
0.6694	Remote Similarity	NPD6869	Approved
0.6694	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6641	Remote Similarity	NPD7604	Phase 2
0.6636	Remote Similarity	NPD4786	Approved
0.6636	Remote Similarity	NPD5328	Approved
0.6614	Remote Similarity	NPD5983	Phase 2
0.6614	Remote Similarity	NPD6921	Approved
0.6583	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD7525	Registered
0.6565	Remote Similarity	NPD6033	Approved
0.6557	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6008	Approved
0.6545	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4788	Approved
0.6542	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3669	Approved
0.6538	Remote Similarity	NPD6336	Discontinued
0.6522	Remote Similarity	NPD4755	Approved
0.6518	Remote Similarity	NPD6079	Approved
0.6514	Remote Similarity	NPD3618	Phase 1
0.65	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7625	Phase 1
0.6476	Remote Similarity	NPD7645	Phase 2
0.6475	Remote Similarity	NPD4634	Approved
0.646	Remote Similarity	NPD4202	Approved
0.6449	Remote Similarity	NPD3667	Approved
0.6436	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5285	Approved
0.641	Remote Similarity	NPD4696	Approved
0.641	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD5286	Approved
0.6408	Remote Similarity	NPD3703	Phase 2
0.6396	Remote Similarity	NPD5737	Approved
0.6396	Remote Similarity	NPD6672	Approved
0.637	Remote Similarity	NPD8449	Approved
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6355	Remote Similarity	NPD1779	Approved
0.6355	Remote Similarity	NPD1780	Approved
0.6349	Remote Similarity	NPD6274	Approved
0.6348	Remote Similarity	NPD5695	Phase 3
0.6328	Remote Similarity	NPD7100	Approved
0.6328	Remote Similarity	NPD7101	Approved
0.6325	Remote Similarity	NPD5696	Approved
0.6325	Remote Similarity	NPD4225	Approved
0.6324	Remote Similarity	NPD8450	Suspended
0.6306	Remote Similarity	NPD7524	Approved
0.6303	Remote Similarity	NPD5225	Approved
0.6303	Remote Similarity	NPD5226	Approved
0.6303	Remote Similarity	NPD4633	Approved
0.6303	Remote Similarity	NPD5224	Approved
0.6303	Remote Similarity	NPD5211	Phase 2
0.6293	Remote Similarity	NPD4697	Phase 3
0.6293	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5222	Approved
0.6293	Remote Similarity	NPD5221	Approved
0.6283	Remote Similarity	NPD46	Approved
0.6283	Remote Similarity	NPD6698	Approved
0.6281	Remote Similarity	NPD4768	Approved
0.6281	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD8338	Approved
0.625	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD3702	Approved
0.625	Remote Similarity	NPD5175	Approved
0.625	Remote Similarity	NPD6903	Approved
0.6241	Remote Similarity	NPD8074	Phase 3
0.6239	Remote Similarity	NPD5173	Approved
0.6238	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6909	Approved
0.6231	Remote Similarity	NPD6908	Approved
0.6228	Remote Similarity	NPD7637	Suspended
0.6228	Remote Similarity	NPD6411	Approved
0.622	Remote Similarity	NPD6868	Approved
0.6218	Remote Similarity	NPD5223	Approved
0.6207	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5141	Approved
0.6195	Remote Similarity	NPD4753	Phase 2
0.6194	Remote Similarity	NPD8336	Approved
0.6194	Remote Similarity	NPD8337	Approved
0.6182	Remote Similarity	NPD3133	Approved
0.6182	Remote Similarity	NPD3666	Approved
0.6182	Remote Similarity	NPD3665	Phase 1
0.6179	Remote Similarity	NPD4730	Approved
0.6179	Remote Similarity	NPD4729	Approved
0.6176	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6317	Approved
0.6134	Remote Similarity	NPD8418	Phase 2
0.6124	Remote Similarity	NPD6313	Approved
0.6124	Remote Similarity	NPD6314	Approved
0.6117	Remote Similarity	NPD6081	Approved
0.6117	Remote Similarity	NPD5777	Approved
0.6116	Remote Similarity	NPD4754	Approved
0.6111	Remote Similarity	NPD6053	Discontinued
0.6103	Remote Similarity	NPD5956	Approved
0.6087	Remote Similarity	NPD7983	Approved
0.6083	Remote Similarity	NPD1700	Approved
0.608	Remote Similarity	NPD5250	Approved
0.608	Remote Similarity	NPD5248	Approved
0.608	Remote Similarity	NPD5247	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