NPASS Compound

Structure

CID71391 OpenBabel06191715412D 82 90 0 0 1 0 0 0 0 0999 V2000 4.2360 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9304 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2053 3.7820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1835 3.7820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8997 -2.8037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8779 -2.8037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7080 -3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1664 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.7080 -4.4022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0136 -0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2360 -3.4239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5416 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6944 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2360 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.8608 -4.8913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0136 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2360 -4.4022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0832 -4.8913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0136 -4.4022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9304 -4.4022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6248 -0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6248 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7776 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1664 -1.9565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7776 -1.9565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8472 -0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6944 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7776 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0136 -3.4239 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9304 -3.4239 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3192 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9304 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6944 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -0.4891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8472 -0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6944 0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5416 -3.4239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.5552 -4.8913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8608 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8608 -5.8696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8608 -1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -4.8913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0832 -5.8696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1664 -4.8913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7776 -4.8913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4720 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6248 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9304 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 2.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8608 -2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3192 -0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0832 -2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 0.9783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0832 -1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4720 -1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9304 -0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1664 -2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7776 -2.9348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 23 1 0 0 0 0 3 52 1 0 0 0 0 4 52 1 0 0 0 0 5 53 1 0 0 0 0 6 53 1 0 0 0 0 8 55 1 0 0 0 0 10 23 2 0 0 0 0 11 12 1 0 0 0 0 11 24 2 0 0 0 0 12 30 1 0 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 31 1 0 0 0 0 15 54 1 0 0 0 0 16 55 1 0 0 0 0 17 25 1 0 0 0 0 17 52 1 0 0 0 0 18 32 1 0 0 0 0 18 52 1 0 0 0 0 19 58 1 0 0 0 0 20 26 1 0 0 0 0 20 74 1 0 0 0 0 21 27 1 0 0 0 0 21 75 1 0 0 0 0 22 59 1 0 0 0 0 23 47 1 0 0 0 0 24 25 1 0 0 0 0 24 56 1 0 0 0 0 25 57 1 6 0 0 0 26 33 1 0 0 0 0 26 60 1 6 0 0 0 27 34 1 0 0 0 0 27 61 1 1 0 0 0 28 19 1 6 0 0 0 28 35 1 0 0 0 0 28 76 1 0 0 0 0 29 53 1 0 0 0 0 29 54 1 1 0 0 0 30 54 1 1 0 0 0 30 55 1 0 0 0 0 31 53 1 0 0 0 0 31 78 1 1 0 0 0 32 57 1 6 0 0 0 32 77 1 0 0 0 0 33 37 1 0 0 0 0 33 62 1 1 0 0 0 34 42 1 0 0 0 0 34 63 1 1 0 0 0 35 36 1 0 0 0 0 35 64 1 6 0 0 0 36 38 1 0 0 0 0 36 65 1 6 0 0 0 37 48 1 0 0 0 0 37 66 1 6 0 0 0 38 49 1 0 0 0 0 38 67 1 1 0 0 0 39 40 1 0 0 0 0 39 41 1 0 0 0 0 39 68 1 6 0 0 0 40 43 1 0 0 0 0 40 79 1 1 0 0 0 41 46 1 1 0 0 0 41 80 1 0 0 0 0 42 50 1 0 0 0 0 42 81 1 6 0 0 0 43 51 1 0 0 0 0 43 82 1 6 0 0 0 44 45 1 0 0 0 0 44 56 1 6 0 0 0 44 69 1 0 0 0 0 45 57 1 6 0 0 0 45 70 1 0 0 0 0 46 71 2 0 0 0 0 46 72 1 0 0 0 0 47 73 2 0 0 0 0 47 77 1 0 0 0 0 48 74 1 0 0 0 0 48 81 1 1 0 0 0 49 76 1 0 0 0 0 49 82 1 6 0 0 0 50 75 1 0 0 0 0 50 79 1 1 0 0 0 51 78 1 1 0 0 0 51 80 1 0 0 0 0 54 7 1 1 0 0 0 55 56 1 6 0 0 0 56 9 1 6 0 0 0 57 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1174.58
Volume:	1126.629
LogP:	1.385
LogD:	1.17
LogS:	-2.821
# Rotatable Bonds:	14
TPSA:	400.43
# H-Bond Aceptor:	25
# H-Bond Donor:	14
# Rings:	9
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.042
Synthetic Accessibility Score:	7.227
Fsp3:	0.895
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:	-6.205
MDCK Permeability:	0.00023977486125659198
Pgp-inhibitor:	0.642
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.987
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.245
Plasma Protein Binding (PPB):	61.015464782714844%
Volume Distribution (VD):	0.086
Pgp-substrate:	12.176946640014648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.03
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.083
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.614
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.131
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC71391

Natural Product ID:	NPC71391
*Common Name:**	Gordonoside J
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9S,12aS,14aR,14bR)-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:	gordonoside J
Standard InCHIKey:	GMMMRIWOKNYPOM-BFYDJWHYSA-N
Standard InCHI:	InChI=1S/C57H90O25/c1-10-23(2)47(73)77-32-18-52(3,4)17-25-24-11-12-30-54(7)15-14-31(53(5,6)29(54)13-16-55(30,8)56(24,9)44(69)45(70)57(25,32)22-59)78-51-43(82-49-38(67)36(65)35(64)28(19-58)76-49)40(39(68)41(80-51)46(71)72)79-50-42(34(63)27(61)21-75-50)81-48-37(66)33(62)26(60)20-74-48/h10-11,25-45,48-51,58-70H,12-22H2,1-9H3,(H,71,72)/b23-10-/t25-,26+,27-,28+,29-,30+,31-,32-,33-,34-,35-,36-,37+,38+,39-,40-,41-,42+,43+,44-,45+,48-,49-,50-,51+,54-,55+,56-,57+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O[C@@H]2OC[C@@H]([C@@H]([C@H]2O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O)O)O)C(=O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)[C@@H](O)[C@H]([C@@]2([C@H]3CC(C)(C)C[C@@H]2OC(=O)/C(=CC)/C)CO)O)C)C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782821
PubChem CID:	54586126
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
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	Roots	Yunnan Province, China	2005-MAY	PMID[20560647]
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	n.a.	stem	n.a.	PMID[21473609]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	9.1	%	PMID[543802]

☑ 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 NPC71391 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	322
0.1-0.2	1889
0.2-0.3	4796
0.3-0.4	8013
0.4-0.5	12035
0.5-0.6	8491
0.6-0.7	4375
0.7-0.8	1933
0.8-0.85	318
0.85-0.9	310
0.9-0.95	123
0.95-1	92

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC192765
1.0	High Similarity	NPC46823
1.0	High Similarity	NPC277212
1.0	High Similarity	NPC178264
1.0	High Similarity	NPC30279
1.0	High Similarity	NPC473918
0.9917	High Similarity	NPC271610
0.9917	High Similarity	NPC225791
0.9917	High Similarity	NPC476780
0.9917	High Similarity	NPC476774
0.9917	High Similarity	NPC476775
0.9835	High Similarity	NPC476776
0.9835	High Similarity	NPC312650
0.9833	High Similarity	NPC141600
0.9833	High Similarity	NPC82380
0.9833	High Similarity	NPC265841
0.9833	High Similarity	NPC115656
0.9833	High Similarity	NPC470518
0.9833	High Similarity	NPC88311
0.9833	High Similarity	NPC470913
0.9833	High Similarity	NPC470912
0.9833	High Similarity	NPC477076
0.9833	High Similarity	NPC269484
0.9833	High Similarity	NPC47995
0.9833	High Similarity	NPC11577
0.9833	High Similarity	NPC252289
0.9833	High Similarity	NPC273878
0.9833	High Similarity	NPC1314
0.9833	High Similarity	NPC107536
0.9833	High Similarity	NPC244296
0.9833	High Similarity	NPC9470
0.9833	High Similarity	NPC252657
0.9833	High Similarity	NPC305793
0.9833	High Similarity	NPC472267
0.9833	High Similarity	NPC280029
0.9833	High Similarity	NPC97918
0.9833	High Similarity	NPC477079
0.9833	High Similarity	NPC477077
0.9752	High Similarity	NPC477197
0.975	High Similarity	NPC329923
0.975	High Similarity	NPC477193
0.975	High Similarity	NPC477192
0.975	High Similarity	NPC477075
0.975	High Similarity	NPC477078
0.975	High Similarity	NPC477191
0.975	High Similarity	NPC475281
0.975	High Similarity	NPC477194
0.9675	High Similarity	NPC476777
0.9675	High Similarity	NPC476778
0.9672	High Similarity	NPC478150
0.9672	High Similarity	NPC478152
0.9672	High Similarity	NPC478153
0.9669	High Similarity	NPC477196
0.9597	High Similarity	NPC110700
0.9597	High Similarity	NPC279915
0.9593	High Similarity	NPC476779
0.9593	High Similarity	NPC478151
0.959	High Similarity	NPC475167
0.959	High Similarity	NPC329993
0.959	High Similarity	NPC475377
0.959	High Similarity	NPC25998
0.959	High Similarity	NPC134914
0.959	High Similarity	NPC172374
0.959	High Similarity	NPC262796
0.959	High Similarity	NPC173435
0.959	High Similarity	NPC478155
0.959	High Similarity	NPC478065
0.959	High Similarity	NPC478064
0.959	High Similarity	NPC476074
0.959	High Similarity	NPC301639
0.959	High Similarity	NPC45346
0.959	High Similarity	NPC264566
0.9512	High Similarity	NPC478154
0.9512	High Similarity	NPC477195
0.9426	High Similarity	NPC470475
0.9344	High Similarity	NPC470516
0.9339	High Similarity	NPC23275
0.9268	High Similarity	NPC470476
0.9256	High Similarity	NPC257211
0.925	High Similarity	NPC187618
0.925	High Similarity	NPC302887
0.918	High Similarity	NPC247315
0.918	High Similarity	NPC33068
0.918	High Similarity	NPC471962
0.918	High Similarity	NPC471963
0.9174	High Similarity	NPC4749
0.9174	High Similarity	NPC475591
0.9174	High Similarity	NPC213952
0.9174	High Similarity	NPC10607
0.9174	High Similarity	NPC21691
0.9174	High Similarity	NPC313110
0.9174	High Similarity	NPC236870
0.9174	High Similarity	NPC131469
0.9174	High Similarity	NPC80986
0.9174	High Similarity	NPC187290
0.9167	High Similarity	NPC118440
0.9167	High Similarity	NPC236657
0.9106	High Similarity	NPC284449
0.9106	High Similarity	NPC181066
0.9106	High Similarity	NPC469947
0.9098	High Similarity	NPC258617
0.9098	High Similarity	NPC202666
0.9098	High Similarity	NPC478066
0.9098	High Similarity	NPC283417
0.9098	High Similarity	NPC200049
0.9098	High Similarity	NPC471964
0.9098	High Similarity	NPC14617
0.9098	High Similarity	NPC302543
0.9098	High Similarity	NPC262199
0.9098	High Similarity	NPC471961
0.9091	High Similarity	NPC114484
0.9091	High Similarity	NPC22956
0.9091	High Similarity	NPC171544
0.9091	High Similarity	NPC223301
0.9091	High Similarity	NPC62725
0.9091	High Similarity	NPC297263
0.9091	High Similarity	NPC86222
0.9091	High Similarity	NPC11242
0.9091	High Similarity	NPC159309
0.9091	High Similarity	NPC301449
0.9091	High Similarity	NPC31838
0.9091	High Similarity	NPC64715
0.9091	High Similarity	NPC104372
0.9091	High Similarity	NPC222580
0.9024	High Similarity	NPC470477
0.9024	High Similarity	NPC160452
0.9016	High Similarity	NPC162574
0.9016	High Similarity	NPC471965
0.9	High Similarity	NPC470515
0.8992	High Similarity	NPC596
0.8968	High Similarity	NPC300655
0.8968	High Similarity	NPC222951
0.8968	High Similarity	NPC43589
0.8968	High Similarity	NPC311178
0.896	High Similarity	NPC23020
0.896	High Similarity	NPC472269
0.896	High Similarity	NPC112492
0.896	High Similarity	NPC472268
0.896	High Similarity	NPC472270
0.8952	High Similarity	NPC470218
0.8952	High Similarity	NPC475368
0.8952	High Similarity	NPC285091
0.8943	High Similarity	NPC30735
0.8943	High Similarity	NPC235405
0.8943	High Similarity	NPC281148
0.8943	High Similarity	NPC2370
0.8943	High Similarity	NPC44716
0.8934	High Similarity	NPC75417
0.8926	High Similarity	NPC208381
0.8926	High Similarity	NPC214484
0.8926	High Similarity	NPC469945
0.8926	High Similarity	NPC6377
0.8926	High Similarity	NPC309780
0.8926	High Similarity	NPC11551
0.8926	High Similarity	NPC470911
0.8926	High Similarity	NPC180550
0.8926	High Similarity	NPC473884
0.8926	High Similarity	NPC470517
0.8926	High Similarity	NPC475171
0.8926	High Similarity	NPC470915
0.8926	High Similarity	NPC157868
0.8926	High Similarity	NPC39211
0.8926	High Similarity	NPC35405
0.8926	High Similarity	NPC472949
0.8926	High Similarity	NPC114441
0.8926	High Similarity	NPC192791
0.8917	High Similarity	NPC224121
0.8915	High Similarity	NPC190065
0.8915	High Similarity	NPC141215
0.8915	High Similarity	NPC471089
0.8898	High Similarity	NPC473679
0.8898	High Similarity	NPC475444
0.8898	High Similarity	NPC196874
0.8898	High Similarity	NPC475177
0.8898	High Similarity	NPC233223
0.8898	High Similarity	NPC324933
0.8898	High Similarity	NPC183816
0.8898	High Similarity	NPC319719
0.8898	High Similarity	NPC322904
0.8862	High Similarity	NPC40775
0.8862	High Similarity	NPC107966
0.8862	High Similarity	NPC249848
0.8862	High Similarity	NPC235438
0.8846	High Similarity	NPC140045
0.8846	High Similarity	NPC295885
0.8843	High Similarity	NPC471548
0.8843	High Similarity	NPC286347
0.8837	High Similarity	NPC262813
0.881	High Similarity	NPC45606
0.881	High Similarity	NPC220838
0.88	High Similarity	NPC297950
0.878	High Similarity	NPC31193
0.878	High Similarity	NPC242840
0.877	High Similarity	NPC473401
0.877	High Similarity	NPC470914
0.8769	High Similarity	NPC251998
0.876	High Similarity	NPC300419
0.876	High Similarity	NPC475119
0.876	High Similarity	NPC473405
0.876	High Similarity	NPC473824

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 NPC71391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	2077
0.2-0.3	3712
0.3-0.4	1962
0.4-0.5	658
0.5-0.6	284
0.6-0.7	120
0.7-0.8	29
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9098	High Similarity	NPD8328	Phase 3
0.876	High Similarity	NPD8295	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD8517	Approved
0.8047	Intermediate Similarity	NPD8515	Approved
0.8047	Intermediate Similarity	NPD8516	Approved
0.7907	Intermediate Similarity	NPD8513	Phase 3
0.7895	Intermediate Similarity	NPD7319	Approved
0.7829	Intermediate Similarity	NPD8377	Approved
0.7829	Intermediate Similarity	NPD8294	Approved
0.782	Intermediate Similarity	NPD7736	Approved
0.7805	Intermediate Similarity	NPD6686	Approved
0.7803	Intermediate Similarity	NPD7507	Approved
0.7778	Intermediate Similarity	NPD8133	Approved
0.7769	Intermediate Similarity	NPD8033	Approved
0.7769	Intermediate Similarity	NPD8296	Approved
0.7769	Intermediate Similarity	NPD8380	Approved
0.7769	Intermediate Similarity	NPD8335	Approved
0.7769	Intermediate Similarity	NPD8379	Approved
0.7769	Intermediate Similarity	NPD8378	Approved
0.7742	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD8293	Discontinued
0.7481	Intermediate Similarity	NPD7516	Approved
0.7444	Intermediate Similarity	NPD6370	Approved
0.7405	Intermediate Similarity	NPD7328	Approved
0.7405	Intermediate Similarity	NPD7327	Approved
0.7381	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7503	Approved
0.7344	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7492	Approved
0.7293	Intermediate Similarity	NPD6054	Approved
0.7293	Intermediate Similarity	NPD6319	Approved
0.7279	Intermediate Similarity	NPD6616	Approved
0.7226	Intermediate Similarity	NPD7078	Approved
0.7197	Intermediate Similarity	NPD7115	Discovery
0.7165	Intermediate Similarity	NPD6412	Phase 2
0.7164	Intermediate Similarity	NPD6059	Approved
0.7154	Intermediate Similarity	NPD8297	Approved
0.7154	Intermediate Similarity	NPD4225	Approved
0.7154	Intermediate Similarity	NPD6882	Approved
0.7111	Intermediate Similarity	NPD6015	Approved
0.7111	Intermediate Similarity	NPD6016	Approved
0.7073	Intermediate Similarity	NPD7902	Approved
0.7068	Intermediate Similarity	NPD6009	Approved
0.7059	Intermediate Similarity	NPD5988	Approved
0.7016	Intermediate Similarity	NPD7638	Approved
0.6978	Remote Similarity	NPD8074	Phase 3
0.6967	Remote Similarity	NPD7748	Approved
0.696	Remote Similarity	NPD7640	Approved
0.696	Remote Similarity	NPD7639	Approved
0.6947	Remote Similarity	NPD6650	Approved
0.6947	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6923	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6921	Approved
0.6846	Remote Similarity	NPD6881	Approved
0.6846	Remote Similarity	NPD6899	Approved
0.6842	Remote Similarity	NPD4632	Approved
0.6829	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7900	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6803	Remote Similarity	NPD7515	Phase 2
0.6769	Remote Similarity	NPD5697	Approved
0.6746	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6883	Approved
0.6742	Remote Similarity	NPD7290	Approved
0.6742	Remote Similarity	NPD7102	Approved
0.6718	Remote Similarity	NPD7320	Approved
0.6692	Remote Similarity	NPD6847	Approved
0.6692	Remote Similarity	NPD6617	Approved
0.6692	Remote Similarity	NPD6869	Approved
0.669	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6643	Remote Similarity	NPD7604	Phase 2
0.6643	Remote Similarity	NPD7829	Approved
0.6643	Remote Similarity	NPD7830	Approved
0.6641	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5701	Approved
0.6619	Remote Similarity	NPD5983	Phase 2
0.6617	Remote Similarity	NPD4634	Approved
0.6615	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6011	Approved
0.6587	Remote Similarity	NPD7799	Discontinued
0.6585	Remote Similarity	NPD46	Approved
0.6585	Remote Similarity	NPD6698	Approved
0.6554	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7260	Phase 2
0.6549	Remote Similarity	NPD6336	Discontinued
0.6512	Remote Similarity	NPD5344	Discontinued
0.6503	Remote Similarity	NPD8448	Approved
0.6486	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD8391	Approved
0.6483	Remote Similarity	NPD8390	Approved
0.6483	Remote Similarity	NPD8392	Approved
0.6462	Remote Similarity	NPD7632	Discontinued
0.6444	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8451	Approved
0.6433	Remote Similarity	NPD8368	Discontinued
0.6419	Remote Similarity	NPD8415	Approved
0.64	Remote Similarity	NPD6411	Approved
0.64	Remote Similarity	NPD7983	Approved
0.6387	Remote Similarity	NPD7625	Phase 1
0.6377	Remote Similarity	NPD6274	Approved
0.637	Remote Similarity	NPD6371	Approved
0.6357	Remote Similarity	NPD7101	Approved
0.6357	Remote Similarity	NPD7100	Approved
0.6349	Remote Similarity	NPD5778	Approved
0.6349	Remote Similarity	NPD5779	Approved
0.6338	Remote Similarity	NPD8080	Discontinued
0.6336	Remote Similarity	NPD5211	Phase 2
0.6322	Remote Similarity	NPD8407	Phase 2
0.632	Remote Similarity	NPD7838	Discovery
0.6316	Remote Similarity	NPD6008	Approved
0.6308	Remote Similarity	NPD5286	Approved
0.6308	Remote Similarity	NPD5285	Approved
0.6308	Remote Similarity	NPD4696	Approved
0.6294	Remote Similarity	NPD6067	Discontinued
0.6294	Remote Similarity	NPD7642	Approved
0.6286	Remote Similarity	NPD6335	Approved
0.6284	Remote Similarity	NPD6845	Suspended
0.6279	Remote Similarity	NPD6084	Phase 2
0.6279	Remote Similarity	NPD4755	Approved
0.6279	Remote Similarity	NPD6083	Phase 2
0.6277	Remote Similarity	NPD6053	Discontinued
0.627	Remote Similarity	NPD8035	Phase 2
0.627	Remote Similarity	NPD8034	Phase 2
0.6268	Remote Similarity	NPD8444	Approved
0.6259	Remote Similarity	NPD6868	Approved
0.6257	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8299	Approved
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD8341	Approved
0.625	Remote Similarity	NPD8340	Approved
0.6241	Remote Similarity	NPD5141	Approved
0.624	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6101	Approved
0.622	Remote Similarity	NPD6399	Phase 3
0.6214	Remote Similarity	NPD6317	Approved
0.6212	Remote Similarity	NPD5225	Approved
0.6212	Remote Similarity	NPD5226	Approved
0.6212	Remote Similarity	NPD5224	Approved
0.6212	Remote Similarity	NPD4633	Approved
0.621	Remote Similarity	NPD3573	Approved
0.6202	Remote Similarity	NPD4697	Phase 3
0.6202	Remote Similarity	NPD5221	Approved
0.6202	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5222	Approved
0.6201	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4700	Approved
0.6183	Remote Similarity	NPD6648	Approved
0.618	Remote Similarity	NPD8435	Approved
0.617	Remote Similarity	NPD6313	Approved
0.617	Remote Similarity	NPD6314	Approved
0.6165	Remote Similarity	NPD5175	Approved
0.6165	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6909	Approved
0.6154	Remote Similarity	NPD6908	Approved
0.6149	Remote Similarity	NPD5956	Approved
0.6142	Remote Similarity	NPD6079	Approved
0.6141	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5223	Approved
0.6133	Remote Similarity	NPD8450	Suspended
0.6124	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8337	Approved
0.6122	Remote Similarity	NPD8336	Approved
0.6111	Remote Similarity	NPD5328	Approved
0.6111	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD5696	Approved
0.6103	Remote Similarity	NPD4729	Approved
0.6103	Remote Similarity	NPD4730	Approved
0.6096	Remote Similarity	NPD8320	Phase 1
0.6096	Remote Similarity	NPD8319	Approved
0.6094	Remote Similarity	NPD8171	Discontinued
0.6089	Remote Similarity	NPD8361	Approved
0.6089	Remote Similarity	NPD8360	Approved
0.6083	Remote Similarity	NPD7329	Approved
0.6083	Remote Similarity	NPD7645	Phase 2
0.608	Remote Similarity	NPD8312	Approved
0.608	Remote Similarity	NPD8313	Approved
0.6077	Remote Similarity	NPD7839	Suspended
0.6074	Remote Similarity	NPD4767	Approved
0.6074	Remote Similarity	NPD4768	Approved
0.6067	Remote Similarity	NPD8449	Approved
0.6067	Remote Similarity	NPD8338	Approved
0.6067	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7641	Discontinued
0.6042	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5737	Approved
0.6032	Remote Similarity	NPD6672	Approved
0.6014	Remote Similarity	NPD5250	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