NPASS Compound

Structure

NPC189704 OpenBabel07101718322D 86 94 0 0 1 0 0 0 0 0999 V2000 1.6057 4.9418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7647 3.6547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0705 3.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2784 2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2094 -5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6113 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8136 3.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5352 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0878 -5.1391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0878 -3.4071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2094 -4.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7453 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5878 -4.2731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.0754 -4.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7453 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.0754 -3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8793 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.2094 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0132 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5878 -2.5411 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0878 -3.4071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3434 -3.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0132 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0878 -3.4071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 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 -11.3434 -6.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4158 1.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -6.0052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -4.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5878 -4.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.9414 -4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6113 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.9414 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2094 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 -3.4071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -4.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4773 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3434 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 4 28 1 0 0 0 0 6 59 1 0 0 0 0 7 75 1 0 0 0 0 8 76 1 0 0 0 0 9 13 1 0 0 0 0 9 26 1 0 0 0 0 10 14 2 0 0 0 0 10 29 1 0 0 0 0 11 12 1 0 0 0 0 11 30 2 0 0 0 0 13 35 1 0 0 0 0 14 38 1 0 0 0 0 15 17 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 16 33 1 0 0 0 0 17 58 1 0 0 0 0 18 59 1 0 0 0 0 19 29 2 0 0 0 0 19 39 1 0 0 0 0 20 30 1 0 0 0 0 20 31 1 0 0 0 0 21 34 1 0 0 0 0 21 42 1 0 0 0 0 22 61 1 0 0 0 0 23 36 1 0 0 0 0 23 77 1 0 0 0 0 24 37 1 0 0 0 0 24 78 1 0 0 0 0 25 79 1 0 0 0 0 27 3 1 1 0 0 0 27 35 1 0 0 0 0 27 60 1 0 0 0 0 28 62 2 0 0 0 0 28 80 1 0 0 0 0 29 53 1 0 0 0 0 30 58 1 0 0 0 0 31 81 1 1 0 0 0 32 12 1 6 0 0 0 32 33 1 0 0 0 0 32 34 1 0 0 0 0 33 58 1 1 0 0 0 34 59 1 1 0 0 0 35 63 2 0 0 0 0 36 43 1 0 0 0 0 36 64 1 6 0 0 0 37 50 1 0 0 0 0 37 65 1 1 0 0 0 38 39 2 0 0 0 0 38 75 1 0 0 0 0 39 76 1 0 0 0 0 40 22 1 6 0 0 0 40 44 1 0 0 0 0 40 82 1 0 0 0 0 41 25 1 6 0 0 0 41 45 1 0 0 0 0 41 83 1 0 0 0 0 42 60 1 1 0 0 0 42 84 1 0 0 0 0 43 51 1 0 0 0 0 43 66 1 1 0 0 0 44 46 1 0 0 0 0 44 67 1 1 0 0 0 45 47 1 0 0 0 0 45 68 1 1 0 0 0 46 48 1 0 0 0 0 46 69 1 6 0 0 0 47 49 1 0 0 0 0 47 70 1 6 0 0 0 48 54 1 0 0 0 0 48 71 1 1 0 0 0 49 55 1 0 0 0 0 49 72 1 1 0 0 0 50 52 1 0 0 0 0 50 86 1 1 0 0 0 51 56 1 0 0 0 0 51 85 1 6 0 0 0 52 57 1 0 0 0 0 52 80 1 6 0 0 0 53 73 2 0 0 0 0 53 85 1 0 0 0 0 54 79 1 6 0 0 0 54 82 1 0 0 0 0 55 81 1 6 0 0 0 55 83 1 0 0 0 0 56 77 1 0 0 0 0 56 86 1 1 0 0 0 57 78 1 0 0 0 0 57 84 1 1 0 0 0 58 5 1 1 0 0 0 59 60 1 6 0 0 0 60 74 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1226.57
Volume:	1179.398
LogP:	2.503
LogD:	1.328
LogS:	-3.41
# Rotatable Bonds:	22
TPSA:	384.5
# H-Bond Aceptor:	26
# H-Bond Donor:	11
# Rings:	9
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	7.02
Fsp3:	0.817
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:	-6.088
MDCK Permeability:	0.00037641270318999887
Pgp-inhibitor:	0.662
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.985
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	66.84488677978516%
Volume Distribution (VD):	0.191
Pgp-substrate:	16.811803817749023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	0.61
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.669
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.348
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.149
Carcinogencity:	0.2
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.802

Download Data

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

Natural Product: NPC189704

Natural Product ID:	NPC189704
*Common Name:**	3Beta-[(O-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl)Oxy)]-17Alpha-Hydroxy-16Beta-[(O-(2-O-3,4-Dimethoxybenzoyl-Beta-D-Xylopyranosyl)-(1->3)-2-O-Acetyl-Alpha-L-Arabinopyranosyl)Oxy]Cholest-5-En-22-One
IUPAC Name:	[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-5-hydroxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-hydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] 3,4-dimethoxybenzoate
Synonyms:
Standard InCHIKey:	QYISKDXFGLVJKT-OWPHNVFYSA-N
Standard InCHI:	InChI=1S/C60H90O26/c1-26(2)9-13-35(63)27(3)60(74)42(84-57-52(80-28(4)62)50(37(65)24-78-57)86-56-51(43(66)36(64)23-77-56)85-53(73)29-10-14-38(75-7)39(19-29)76-8)21-34-32-12-11-30-20-31(15-17-58(30,5)33(32)16-18-59(34,60)6)81-55-49(72)47(70)45(68)41(83-55)25-79-54-48(71)46(69)44(67)40(22-61)82-54/h10-11,14,19,26-27,31-34,36-37,40-52,54-57,61,64-72,74H,9,12-13,15-18,20-25H2,1-8H3/t27-,31+,32-,33+,34+,36-,37+,40-,41-,42+,43+,44-,45-,46+,47+,48-,49-,50+,51-,52-,54-,55-,56+,57+,58+,59+,60-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H]3CC[C@]4(C(=CC[C@@H]5[C@@H]4CC[C@]4([C@H]5C[C@@H]([C@]4(O)[C@@H](C(=O)CCC(C)C)C)O[C@@H]4OC[C@@H]([C@@H]([C@H]4OC(=O)C)O[C@@H]4OC[C@H]([C@@H]([C@H]4OC(=O)c4ccc(c(c4)OC)OC)O)O)O)C)C3)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501237
PubChem CID:	10986051
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[12398536]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	n.a.	bulb	n.a.	PMID[12398536]
NPO29813	Ornithogalum thyrsoides	Species	Hyacinthaceae	Eukaryota	bulbs	n.a.	n.a.	PMID[15497941]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.81	ug.mL-1	PMID[572481]

☑ 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 NPC189704 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	431
0.1-0.2	1651
0.2-0.3	3118
0.3-0.4	6072
0.4-0.5	9522
0.5-0.6	9048
0.6-0.7	9390
0.7-0.8	3251
0.8-0.85	150
0.85-0.9	46
0.9-0.95	4
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9942	High Similarity	NPC475121
0.9942	High Similarity	NPC476067
0.9941	High Similarity	NPC96194
0.9941	High Similarity	NPC299855
0.977	High Similarity	NPC475299
0.9713	High Similarity	NPC112708
0.9657	High Similarity	NPC473711
0.9655	High Similarity	NPC230670
0.9655	High Similarity	NPC71385
0.9471	High Similarity	NPC195972
0.9148	High Similarity	NPC473776
0.9148	High Similarity	NPC473205
0.8743	High Similarity	NPC21956
0.8736	High Similarity	NPC282551
0.8708	High Similarity	NPC475613
0.8663	High Similarity	NPC474936
0.8644	High Similarity	NPC469777
0.8644	High Similarity	NPC469772
0.8644	High Similarity	NPC135334
0.8644	High Similarity	NPC469773
0.8644	High Similarity	NPC469775
0.8644	High Similarity	NPC100925
0.8644	High Similarity	NPC469774
0.8644	High Similarity	NPC32723
0.8644	High Similarity	NPC469778
0.8644	High Similarity	NPC469776
0.8644	High Similarity	NPC295941
0.8621	High Similarity	NPC100420
0.8596	High Similarity	NPC124828
0.8563	High Similarity	NPC206815
0.8547	High Similarity	NPC475244
0.8539	High Similarity	NPC470685
0.8531	High Similarity	NPC266545
0.8531	High Similarity	NPC202428
0.8523	High Similarity	NPC200726
0.8523	High Similarity	NPC477488
0.8514	High Similarity	NPC109990
0.8492	Intermediate Similarity	NPC475197
0.8492	Intermediate Similarity	NPC473467
0.8483	Intermediate Similarity	NPC472803
0.8475	Intermediate Similarity	NPC177362
0.8475	Intermediate Similarity	NPC286809
0.8466	Intermediate Similarity	NPC318472
0.8462	Intermediate Similarity	NPC188217
0.8457	Intermediate Similarity	NPC145847
0.8457	Intermediate Similarity	NPC476011
0.8444	Intermediate Similarity	NPC469354
0.843	Intermediate Similarity	NPC476784
0.8418	Intermediate Similarity	NPC130730
0.8418	Intermediate Similarity	NPC469419
0.8418	Intermediate Similarity	NPC301910
0.8409	Intermediate Similarity	NPC327694
0.8391	Intermediate Similarity	NPC179914
0.8372	Intermediate Similarity	NPC476364
0.8362	Intermediate Similarity	NPC102465
0.8352	Intermediate Similarity	NPC469418
0.8352	Intermediate Similarity	NPC473468
0.8352	Intermediate Similarity	NPC246024
0.8352	Intermediate Similarity	NPC475567
0.8352	Intermediate Similarity	NPC473557
0.8352	Intermediate Similarity	NPC477491
0.8352	Intermediate Similarity	NPC326278
0.8343	Intermediate Similarity	NPC469438
0.8333	Intermediate Similarity	NPC13989
0.8333	Intermediate Similarity	NPC471878
0.8315	Intermediate Similarity	NPC473883
0.8315	Intermediate Similarity	NPC186746
0.8305	Intermediate Similarity	NPC475531
0.8305	Intermediate Similarity	NPC475198
0.8305	Intermediate Similarity	NPC475175
0.8304	Intermediate Similarity	NPC475379
0.8297	Intermediate Similarity	NPC475054
0.8297	Intermediate Similarity	NPC469397
0.8295	Intermediate Similarity	NPC477627
0.8287	Intermediate Similarity	NPC471871
0.8287	Intermediate Similarity	NPC316539
0.8278	Intermediate Similarity	NPC52598
0.8258	Intermediate Similarity	NPC180586
0.8251	Intermediate Similarity	NPC475261
0.8239	Intermediate Similarity	NPC476337
0.8239	Intermediate Similarity	NPC130489
0.8239	Intermediate Similarity	NPC208676
0.8232	Intermediate Similarity	NPC477617
0.8232	Intermediate Similarity	NPC148185
0.8229	Intermediate Similarity	NPC187205
0.8229	Intermediate Similarity	NPC268602
0.8229	Intermediate Similarity	NPC226759
0.8222	Intermediate Similarity	NPC471870
0.8222	Intermediate Similarity	NPC61791
0.8218	Intermediate Similarity	NPC475484
0.8208	Intermediate Similarity	NPC137813
0.8207	Intermediate Similarity	NPC108191
0.8207	Intermediate Similarity	NPC275690
0.8207	Intermediate Similarity	NPC93685
0.8207	Intermediate Similarity	NPC473895
0.8207	Intermediate Similarity	NPC161609
0.8202	Intermediate Similarity	NPC120012
0.8202	Intermediate Similarity	NPC161151
0.8187	Intermediate Similarity	NPC199357
0.8182	Intermediate Similarity	NPC475536
0.8182	Intermediate Similarity	NPC165234
0.8182	Intermediate Similarity	NPC68619
0.8177	Intermediate Similarity	NPC131405
0.8177	Intermediate Similarity	NPC472129
0.8177	Intermediate Similarity	NPC43434
0.8176	Intermediate Similarity	NPC476338
0.8176	Intermediate Similarity	NPC476359
0.8172	Intermediate Similarity	NPC167045
0.8172	Intermediate Similarity	NPC114120
0.8167	Intermediate Similarity	NPC471859
0.8167	Intermediate Similarity	NPC471860
0.8162	Intermediate Similarity	NPC469371
0.8161	Intermediate Similarity	NPC478232
0.8156	Intermediate Similarity	NPC475738
0.8152	Intermediate Similarity	NPC120952
0.8148	Intermediate Similarity	NPC264302
0.8142	Intermediate Similarity	NPC294149
0.8136	Intermediate Similarity	NPC475464
0.8136	Intermediate Similarity	NPC473797
0.8136	Intermediate Similarity	NPC475437
0.8136	Intermediate Similarity	NPC475300
0.8136	Intermediate Similarity	NPC475505
0.8136	Intermediate Similarity	NPC138993
0.8136	Intermediate Similarity	NPC329960
0.8136	Intermediate Similarity	NPC473641
0.8136	Intermediate Similarity	NPC150893
0.8136	Intermediate Similarity	NPC295408
0.8132	Intermediate Similarity	NPC472638
0.8122	Intermediate Similarity	NPC197708
0.8122	Intermediate Similarity	NPC658
0.8122	Intermediate Similarity	NPC472133
0.8118	Intermediate Similarity	NPC35924
0.8118	Intermediate Similarity	NPC199172
0.8114	Intermediate Similarity	NPC10205
0.8114	Intermediate Similarity	NPC131532
0.8111	Intermediate Similarity	NPC476277
0.8111	Intermediate Similarity	NPC477466
0.8111	Intermediate Similarity	NPC477471
0.8111	Intermediate Similarity	NPC477469
0.8111	Intermediate Similarity	NPC306475
0.8111	Intermediate Similarity	NPC477473
0.8108	Intermediate Similarity	NPC254588
0.8108	Intermediate Similarity	NPC195114
0.8103	Intermediate Similarity	NPC87403
0.8101	Intermediate Similarity	NPC100425
0.8092	Intermediate Similarity	NPC289021
0.8092	Intermediate Similarity	NPC158546
0.8087	Intermediate Similarity	NPC477881
0.8085	Intermediate Similarity	NPC286301
0.8085	Intermediate Similarity	NPC313063
0.8079	Intermediate Similarity	NPC469384
0.8077	Intermediate Similarity	NPC52353
0.8077	Intermediate Similarity	NPC293004
0.8077	Intermediate Similarity	NPC194483
0.8075	Intermediate Similarity	NPC318119
0.8068	Intermediate Similarity	NPC478248
0.8068	Intermediate Similarity	NPC10945
0.8068	Intermediate Similarity	NPC471405
0.8066	Intermediate Similarity	NPC298847
0.8065	Intermediate Similarity	NPC197357
0.8065	Intermediate Similarity	NPC477860
0.8065	Intermediate Similarity	NPC170203
0.8065	Intermediate Similarity	NPC85316
0.8065	Intermediate Similarity	NPC475161
0.8065	Intermediate Similarity	NPC102367
0.8063	Intermediate Similarity	NPC476358
0.8057	Intermediate Similarity	NPC469417
0.8056	Intermediate Similarity	NPC472131
0.8056	Intermediate Similarity	NPC469420
0.8056	Intermediate Similarity	NPC99216
0.8056	Intermediate Similarity	NPC472130
0.8054	Intermediate Similarity	NPC477880
0.8054	Intermediate Similarity	NPC260300
0.8054	Intermediate Similarity	NPC472387
0.8054	Intermediate Similarity	NPC267549
0.8054	Intermediate Similarity	NPC80360
0.8054	Intermediate Similarity	NPC477882
0.8046	Intermediate Similarity	NPC476335
0.8046	Intermediate Similarity	NPC134905
0.8046	Intermediate Similarity	NPC469456
0.8046	Intermediate Similarity	NPC36130
0.8045	Intermediate Similarity	NPC471873
0.8045	Intermediate Similarity	NPC41009
0.8045	Intermediate Similarity	NPC148273
0.8043	Intermediate Similarity	NPC198199
0.8043	Intermediate Similarity	NPC146803
0.8043	Intermediate Similarity	NPC223735
0.8043	Intermediate Similarity	NPC473630
0.8043	Intermediate Similarity	NPC102028
0.8043	Intermediate Similarity	NPC307754
0.8042	Intermediate Similarity	NPC205721
0.8035	Intermediate Similarity	NPC147224
0.8034	Intermediate Similarity	NPC478265
0.8034	Intermediate Similarity	NPC218471
0.8034	Intermediate Similarity	NPC269668
0.8034	Intermediate Similarity	NPC239818
0.8033	Intermediate Similarity	NPC102851
0.8033	Intermediate Similarity	NPC472639
0.8033	Intermediate Similarity	NPC475155
0.8033	Intermediate Similarity	NPC38438

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 NPC189704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	922
0.2-0.3	2001
0.3-0.4	2717
0.4-0.5	1949
0.5-0.6	886
0.6-0.7	260
0.7-0.8	50
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
0.8596	High Similarity	NPD7685	Pre-registration
0.8207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8313	Approved
0.8	Intermediate Similarity	NPD8312	Approved
0.7978	Intermediate Similarity	NPD7074	Phase 3
0.7967	Intermediate Similarity	NPD7799	Discontinued
0.7895	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD8127	Discontinued
0.7884	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7472	Approved
0.7869	Intermediate Similarity	NPD7228	Approved
0.7849	Intermediate Similarity	NPD7808	Phase 3
0.7826	Intermediate Similarity	NPD7054	Approved
0.7796	Intermediate Similarity	NPD7240	Approved
0.7784	Intermediate Similarity	NPD7028	Phase 2
0.7701	Intermediate Similarity	NPD7251	Discontinued
0.7684	Intermediate Similarity	NPD8434	Phase 2
0.7676	Intermediate Similarity	NPD3818	Discontinued
0.7647	Intermediate Similarity	NPD6797	Phase 2
0.7598	Intermediate Similarity	NPD37	Approved
0.7596	Intermediate Similarity	NPD7199	Phase 2
0.7569	Intermediate Similarity	NPD4965	Approved
0.7569	Intermediate Similarity	NPD4966	Approved
0.7569	Intermediate Similarity	NPD4967	Phase 2
0.7566	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6273	Approved
0.7556	Intermediate Similarity	NPD8455	Phase 2
0.754	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7458	Discontinued
0.7527	Intermediate Similarity	NPD7473	Discontinued
0.7514	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD8151	Discontinued
0.7486	Intermediate Similarity	NPD6234	Discontinued
0.7473	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6166	Phase 2
0.7473	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5844	Phase 1
0.7446	Intermediate Similarity	NPD5494	Approved
0.7443	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7783	Phase 2
0.7415	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7497	Discontinued
0.7413	Intermediate Similarity	NPD7435	Discontinued
0.7409	Intermediate Similarity	NPD8150	Discontinued
0.7386	Intermediate Similarity	NPD7236	Approved
0.7377	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD8320	Phase 1
0.7376	Intermediate Similarity	NPD8319	Approved
0.7371	Intermediate Similarity	NPD4628	Phase 3
0.7371	Intermediate Similarity	NPD8166	Discontinued
0.7366	Intermediate Similarity	NPD6232	Discontinued
0.7363	Intermediate Similarity	NPD5760	Phase 2
0.7363	Intermediate Similarity	NPD5761	Phase 2
0.7363	Intermediate Similarity	NPD7819	Suspended
0.733	Intermediate Similarity	NPD6559	Discontinued
0.7327	Intermediate Similarity	NPD7698	Approved
0.7327	Intermediate Similarity	NPD7696	Phase 3
0.7327	Intermediate Similarity	NPD7697	Approved
0.7299	Intermediate Similarity	NPD7266	Discontinued
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7239	Suspended
0.7268	Intermediate Similarity	NPD7701	Phase 2
0.7264	Intermediate Similarity	NPD6777	Approved
0.7264	Intermediate Similarity	NPD6781	Approved
0.7264	Intermediate Similarity	NPD6779	Approved
0.7264	Intermediate Similarity	NPD6776	Approved
0.7264	Intermediate Similarity	NPD6778	Approved
0.7264	Intermediate Similarity	NPD6780	Approved
0.7264	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD3817	Phase 2
0.7213	Intermediate Similarity	NPD1934	Approved
0.7211	Intermediate Similarity	NPD3751	Discontinued
0.7206	Intermediate Similarity	NPD7870	Phase 2
0.7206	Intermediate Similarity	NPD7871	Phase 2
0.7198	Intermediate Similarity	NPD4380	Phase 2
0.7196	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7699	Phase 2
0.7164	Intermediate Similarity	NPD7700	Phase 2
0.7163	Intermediate Similarity	NPD7801	Approved
0.7157	Intermediate Similarity	NPD7680	Approved
0.7151	Intermediate Similarity	NPD7075	Discontinued
0.715	Intermediate Similarity	NPD6764	Approved
0.715	Intermediate Similarity	NPD8368	Discontinued
0.715	Intermediate Similarity	NPD6765	Approved
0.7129	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8407	Phase 2
0.7119	Intermediate Similarity	NPD6674	Discontinued
0.7111	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6823	Phase 2
0.709	Intermediate Similarity	NPD3787	Discontinued
0.7081	Intermediate Similarity	NPD1465	Phase 2
0.7043	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6190	Approved
0.7037	Intermediate Similarity	NPD6959	Discontinued
0.7015	Intermediate Similarity	NPD6535	Approved
0.7015	Intermediate Similarity	NPD6534	Approved
0.7011	Intermediate Similarity	NPD6599	Discontinued
0.7005	Intermediate Similarity	NPD6785	Approved
0.7005	Intermediate Similarity	NPD6784	Approved
0.7005	Intermediate Similarity	NPD7999	Approved
0.7005	Intermediate Similarity	NPD3882	Suspended
0.6995	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2801	Approved
0.6983	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4110	Phase 3
0.6981	Remote Similarity	NPD7930	Approved
0.6973	Remote Similarity	NPD7411	Suspended
0.6957	Remote Similarity	NPD3226	Approved
0.6954	Remote Similarity	NPD3620	Phase 2
0.6954	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4140	Approved
0.6944	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6801	Discontinued
0.6932	Remote Similarity	NPD7097	Phase 1
0.6931	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8404	Phase 2
0.6915	Remote Similarity	NPD7058	Phase 2
0.6915	Remote Similarity	NPD7057	Phase 3
0.6914	Remote Similarity	NPD5735	Approved
0.691	Remote Similarity	NPD5762	Approved
0.691	Remote Similarity	NPD5763	Approved
0.69	Remote Similarity	NPD8361	Approved
0.69	Remote Similarity	NPD8360	Approved
0.69	Remote Similarity	NPD8435	Approved
0.6897	Remote Similarity	NPD8032	Phase 2
0.6862	Remote Similarity	NPD5402	Approved
0.6833	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2534	Approved
0.6831	Remote Similarity	NPD2532	Approved
0.6831	Remote Similarity	NPD2533	Approved
0.6816	Remote Similarity	NPD2346	Discontinued
0.6811	Remote Similarity	NPD1653	Approved
0.68	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6663	Approved
0.6798	Remote Similarity	NPD6213	Phase 3
0.6798	Remote Similarity	NPD6212	Phase 3
0.6798	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7003	Approved
0.6796	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6386	Approved
0.6791	Remote Similarity	NPD6385	Approved
0.6789	Remote Similarity	NPD3749	Approved
0.6784	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6799	Approved
0.6774	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5353	Approved
0.6763	Remote Similarity	NPD5736	Approved
0.6763	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7768	Phase 2
0.6723	Remote Similarity	NPD1933	Approved
0.6723	Remote Similarity	NPD230	Phase 1
0.6712	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD8059	Phase 3
0.6705	Remote Similarity	NPD5647	Approved
0.6704	Remote Similarity	NPD2799	Discontinued
0.6685	Remote Similarity	NPD6653	Approved
0.6685	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1511	Approved
0.6684	Remote Similarity	NPD5978	Approved
0.6684	Remote Similarity	NPD5977	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7296	Approved
0.6667	Remote Similarity	NPD919	Approved
0.6649	Remote Similarity	NPD5401	Approved
0.6649	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD3764	Approved
0.6636	Remote Similarity	NPD7907	Approved
0.6635	Remote Similarity	NPD8285	Discontinued
0.6629	Remote Similarity	NPD447	Suspended
0.6629	Remote Similarity	NPD6355	Discontinued
0.6618	Remote Similarity	NPD8485	Approved
0.6615	Remote Similarity	NPD3926	Phase 2
0.6615	Remote Similarity	NPD5242	Approved
0.6613	Remote Similarity	NPD1512	Approved
0.6612	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3750	Approved
0.6611	Remote Similarity	NPD7033	Discontinued
0.6593	Remote Similarity	NPD1549	Phase 2
0.6592	Remote Similarity	NPD6353	Approved
0.6591	Remote Similarity	NPD7095	Approved
0.6591	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4420	Approved
0.6575	Remote Similarity	NPD2796	Approved
0.6575	Remote Similarity	NPD2438	Suspended
0.6575	Remote Similarity	NPD6099	Approved
0.6575	Remote Similarity	NPD6100	Approved
0.6573	Remote Similarity	NPD7584	Approved
0.6571	Remote Similarity	NPD9494	Approved
0.6564	Remote Similarity	NPD7315	Approved
0.6559	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7422	Clinical (unspecified phase)

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