NPASS Compound

Structure

NPC470514 OpenBabel07101719182D 90 99 0 0 1 0 0 0 0 0999 V2000 -2.3909 3.6337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7922 3.3157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9054 -2.8093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8856 -2.8093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5466 0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8489 -1.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 1.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 -1.9604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2444 -0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3955 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8489 -1.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8489 2.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8489 -0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3376 4.4109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9421 4.4109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1865 -2.9406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6399 0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7910 0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3955 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8489 1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3376 3.4307 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7910 3.9208 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3376 -3.4307 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7910 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7910 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5466 -1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6978 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6978 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2444 -1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1865 2.9406 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6399 4.4109 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3376 -4.4109 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7910 -0.9802 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6399 -0.4901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1865 1.9604 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4888 3.9208 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4888 -4.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9421 -1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6399 -1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3376 1.4703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4888 2.9406 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0933 -0.9802 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6399 -4.4109 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7910 -1.9604 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5466 2.4505 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5466 1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4888 1.9604 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6399 2.4505 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0933 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6399 -3.4307 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9421 -1.4703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6978 2.9406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3955 -1.9604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5466 -0.4901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8489 -0.4901 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 -1.6978 0.9802 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1865 4.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9421 5.3911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0354 -3.4307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5466 -0.4901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0354 3.4307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6399 5.3911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1865 -4.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6399 -1.4703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4888 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0354 1.4703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3376 4.4109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4888 -5.8812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9421 -2.4505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4888 -1.9604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3376 0.4901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3376 2.4505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2444 -1.4703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7910 -4.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3955 2.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3955 0.9802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6399 1.4703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6399 1.4703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2444 0.4901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4888 2.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7910 2.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4888 -2.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9421 0.4901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9421 -0.4901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0933 -1.9604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7910 -2.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 55 1 0 0 0 0 2 55 1 0 0 0 0 3 56 1 0 0 0 0 4 56 1 0 0 0 0 6 58 1 0 0 0 0 8 9 1 0 0 0 0 8 22 2 0 0 0 0 9 30 1 0 0 0 0 10 13 1 0 0 0 0 10 29 1 0 0 0 0 11 12 1 0 0 0 0 11 32 1 0 0 0 0 12 57 1 0 0 0 0 13 58 1 0 0 0 0 14 23 1 0 0 0 0 14 55 1 0 0 0 0 15 31 1 0 0 0 0 15 59 1 0 0 0 0 16 61 1 0 0 0 0 17 62 1 0 0 0 0 18 63 1 0 0 0 0 19 81 1 0 0 0 0 20 82 1 0 0 0 0 21 83 1 0 0 0 0 22 23 1 0 0 0 0 22 59 1 0 0 0 0 23 60 1 1 0 0 0 24 16 1 1 0 0 0 24 33 1 0 0 0 0 24 84 1 0 0 0 0 25 17 1 6 0 0 0 25 34 1 0 0 0 0 25 85 1 0 0 0 0 26 18 1 6 0 0 0 26 35 1 0 0 0 0 26 86 1 0 0 0 0 27 19 1 1 0 0 0 27 36 1 0 0 0 0 27 87 1 0 0 0 0 28 20 1 6 0 0 0 28 37 1 0 0 0 0 28 88 1 0 0 0 0 29 56 1 0 0 0 0 29 57 1 6 0 0 0 30 57 1 6 0 0 0 30 58 1 0 0 0 0 31 60 1 0 0 0 0 31 64 2 0 0 0 0 32 56 1 0 0 0 0 32 89 1 6 0 0 0 33 38 1 0 0 0 0 33 65 1 6 0 0 0 34 39 1 0 0 0 0 34 66 1 1 0 0 0 35 40 1 0 0 0 0 35 67 1 1 0 0 0 36 41 1 0 0 0 0 36 68 1 6 0 0 0 37 42 1 0 0 0 0 37 69 1 1 0 0 0 38 43 1 0 0 0 0 38 70 1 1 0 0 0 39 44 1 0 0 0 0 39 71 1 6 0 0 0 40 46 1 0 0 0 0 40 72 1 6 0 0 0 41 45 1 0 0 0 0 41 73 1 1 0 0 0 42 47 1 0 0 0 0 42 74 1 6 0 0 0 43 50 1 0 0 0 0 43 75 1 6 0 0 0 44 51 1 0 0 0 0 44 76 1 1 0 0 0 45 52 1 0 0 0 0 45 77 1 6 0 0 0 46 53 1 0 0 0 0 46 78 1 1 0 0 0 47 54 1 0 0 0 0 47 90 1 1 0 0 0 48 49 1 0 0 0 0 48 55 1 0 0 0 0 48 79 1 6 0 0 0 49 60 1 1 0 0 0 49 80 1 0 0 0 0 50 81 1 1 0 0 0 50 84 1 0 0 0 0 51 82 1 6 0 0 0 51 85 1 0 0 0 0 52 83 1 1 0 0 0 52 87 1 0 0 0 0 53 86 1 0 0 0 0 53 90 1 6 0 0 0 54 88 1 0 0 0 0 54 89 1 6 0 0 0 57 5 1 6 0 0 0 58 59 1 1 0 0 0 59 7 1 1 0 0 0 60 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1298.61
Volume:	1219.185
LogP:	0.019
LogD:	0.527
LogS:	-2.341
# Rotatable Bonds:	16
TPSA:	493.74
# H-Bond Aceptor:	30
# H-Bond Donor:	19
# Rings:	10
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.05
Synthetic Accessibility Score:	7.488
Fsp3:	0.95
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:	-6.565
MDCK Permeability:	0.00025075278244912624
Pgp-inhibitor:	0.004
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	46.819496154785156%
Volume Distribution (VD):	-0.447
Pgp-substrate:	22.082660675048828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	-0.401
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.191
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.052
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC470514

Natural Product ID:	NPC470514
*Common Name:**	Sorbifoliaside C
IUPAC Name:	(3R,4R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-3,4-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-4a-[[(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]oxymethyl]-3,4,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picen-5-one
Synonyms:	sorbifoliaside C
Standard InCHIKey:	YURMATDASSYCTB-TUANEQDRSA-N
Standard InCHI:	InChI=1S/C60H98O30/c1-55(2)14-23-22-8-9-30-57(5)12-11-32(89-54-47(90-53-46(78)40(72)35(67)26(18-63)86-53)42(74)37(69)28(88-54)20-82-51-44(76)39(71)34(66)25(17-62)85-51)56(3,4)29(57)10-13-58(30,6)59(22,7)15-31(64)60(23,49(80)48(55)79)21-83-52-45(77)41(73)36(68)27(87-52)19-81-50-43(75)38(70)33(65)24(16-61)84-50/h8,23-30,32-54,61-63,65-80H,9-21H2,1-7H3/t23-,24+,25+,26+,27+,28+,29-,30+,32-,33+,34+,35+,36+,37+,38-,39-,40-,41-,42-,43+,44+,45+,46+,47+,48-,49-,50+,51+,52+,53-,54-,57-,58+,59+,60-/m0/s1
SMILES:	CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CC(=O)C2(C(C1O)O)COC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)C)C)(C)C)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2058159
PubChem CID:	66552718
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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]

☑ 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	10

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[490787]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	100000.0	nM	PMID[490787]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[490787]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[490787]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[490787]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[490787]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[490787]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	100000.0	nM	PMID[490787]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[490787]

☑ 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 NPC470514 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	1847
0.2-0.3	5330
0.3-0.4	10653
0.4-0.5	11672
0.5-0.6	6381
0.6-0.7	3730
0.7-0.8	1791
0.8-0.85	389
0.85-0.9	231
0.9-0.95	349
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470513
0.9636	High Similarity	NPC237191
0.955	High Similarity	NPC471577
0.9545	High Similarity	NPC220160
0.9545	High Similarity	NPC191827
0.9545	High Similarity	NPC102505
0.9545	High Similarity	NPC473824
0.9545	High Similarity	NPC475514
0.9545	High Similarity	NPC33012
0.9545	High Similarity	NPC69811
0.9545	High Similarity	NPC470876
0.9545	High Similarity	NPC104137
0.9545	High Similarity	NPC123522
0.9545	High Similarity	NPC85154
0.9545	High Similarity	NPC471580
0.9545	High Similarity	NPC286457
0.9545	High Similarity	NPC475119
0.9545	High Similarity	NPC473452
0.9545	High Similarity	NPC8524
0.9545	High Similarity	NPC309223
0.9545	High Similarity	NPC475209
0.9545	High Similarity	NPC300419
0.9455	High Similarity	NPC305267
0.9455	High Similarity	NPC26626
0.9455	High Similarity	NPC291903
0.9455	High Similarity	NPC288205
0.9455	High Similarity	NPC75287
0.9455	High Similarity	NPC37134
0.9455	High Similarity	NPC51465
0.9455	High Similarity	NPC476992
0.9381	High Similarity	NPC275225
0.9381	High Similarity	NPC51099
0.9381	High Similarity	NPC293031
0.9381	High Similarity	NPC68767
0.9375	High Similarity	NPC473386
0.9375	High Similarity	NPC207738
0.9369	High Similarity	NPC148417
0.9369	High Similarity	NPC136768
0.9369	High Similarity	NPC110633
0.9364	High Similarity	NPC123199
0.9364	High Similarity	NPC71065
0.9364	High Similarity	NPC4328
0.9364	High Similarity	NPC471385
0.9364	High Similarity	NPC309907
0.9364	High Similarity	NPC65105
0.9364	High Similarity	NPC119592
0.9364	High Similarity	NPC100639
0.9364	High Similarity	NPC475160
0.9364	High Similarity	NPC294453
0.9364	High Similarity	NPC54636
0.9364	High Similarity	NPC298034
0.9364	High Similarity	NPC293330
0.9364	High Similarity	NPC57484
0.9364	High Similarity	NPC161717
0.9364	High Similarity	NPC227551
0.9364	High Similarity	NPC79643
0.9364	High Similarity	NPC76972
0.9364	High Similarity	NPC471550
0.9364	High Similarity	NPC204414
0.9364	High Similarity	NPC224381
0.9364	High Similarity	NPC41061
0.9364	High Similarity	NPC469782
0.9364	High Similarity	NPC164389
0.9364	High Similarity	NPC70809
0.9364	High Similarity	NPC236638
0.9364	High Similarity	NPC250247
0.9364	High Similarity	NPC202828
0.9364	High Similarity	NPC305981
0.9364	High Similarity	NPC475486
0.9364	High Similarity	NPC476068
0.9364	High Similarity	NPC475140
0.9364	High Similarity	NPC43550
0.9364	High Similarity	NPC60557
0.9364	High Similarity	NPC473714
0.9364	High Similarity	NPC67857
0.9364	High Similarity	NPC261506
0.9304	High Similarity	NPC33068
0.9292	High Similarity	NPC142151
0.9292	High Similarity	NPC476991
0.9292	High Similarity	NPC153673
0.9292	High Similarity	NPC37860
0.9292	High Similarity	NPC144644
0.9292	High Similarity	NPC473645
0.9292	High Similarity	NPC110385
0.9292	High Similarity	NPC267694
0.9286	High Similarity	NPC473459
0.9286	High Similarity	NPC105800
0.9286	High Similarity	NPC36831
0.9286	High Similarity	NPC232237
0.9279	High Similarity	NPC161674
0.9279	High Similarity	NPC471384
0.9273	High Similarity	NPC46665
0.9273	High Similarity	NPC133818
0.9273	High Similarity	NPC192600
0.9273	High Similarity	NPC475467
0.9273	High Similarity	NPC473826
0.9273	High Similarity	NPC219180
0.9273	High Similarity	NPC166422
0.9273	High Similarity	NPC73318
0.9273	High Similarity	NPC150400
0.9273	High Similarity	NPC134835
0.9273	High Similarity	NPC163183
0.9273	High Similarity	NPC155410
0.9273	High Similarity	NPC238935
0.9273	High Similarity	NPC475208
0.9273	High Similarity	NPC114304
0.9273	High Similarity	NPC96641
0.9273	High Similarity	NPC475287
0.9273	High Similarity	NPC174720
0.9273	High Similarity	NPC241909
0.9273	High Similarity	NPC295823
0.9273	High Similarity	NPC114287
0.9273	High Similarity	NPC151543
0.9273	High Similarity	NPC309714
0.9273	High Similarity	NPC251263
0.9273	High Similarity	NPC323341
0.9273	High Similarity	NPC473343
0.9217	High Similarity	NPC283417
0.9217	High Similarity	NPC302543
0.9217	High Similarity	NPC258617
0.9217	High Similarity	NPC200049
0.9217	High Similarity	NPC257211
0.9204	High Similarity	NPC477464
0.9204	High Similarity	NPC51564
0.9204	High Similarity	NPC135849
0.9204	High Similarity	NPC25663
0.9196	High Similarity	NPC185466
0.9196	High Similarity	NPC323359
0.9196	High Similarity	NPC68175
0.9182	High Similarity	NPC1046
0.9182	High Similarity	NPC292677
0.9182	High Similarity	NPC10320
0.9182	High Similarity	NPC475504
0.9182	High Similarity	NPC109079
0.9182	High Similarity	NPC469946
0.9182	High Similarity	NPC471383
0.9182	High Similarity	NPC473373
0.9182	High Similarity	NPC473383
0.9182	High Similarity	NPC48249
0.9182	High Similarity	NPC80843
0.9182	High Similarity	NPC79718
0.9182	High Similarity	NPC101744
0.9182	High Similarity	NPC139894
0.9182	High Similarity	NPC139044
0.9182	High Similarity	NPC104071
0.9182	High Similarity	NPC324875
0.9182	High Similarity	NPC257468
0.9182	High Similarity	NPC104400
0.9182	High Similarity	NPC475516
0.9182	High Similarity	NPC276093
0.9182	High Similarity	NPC102439
0.9145	High Similarity	NPC470516
0.913	High Similarity	NPC10607
0.913	High Similarity	NPC21691
0.913	High Similarity	NPC475591
0.913	High Similarity	NPC187290
0.913	High Similarity	NPC213952
0.913	High Similarity	NPC313110
0.913	High Similarity	NPC80986
0.913	High Similarity	NPC236870
0.913	High Similarity	NPC131469
0.913	High Similarity	NPC4749
0.913	High Similarity	NPC162574
0.9123	High Similarity	NPC268184
0.9115	High Similarity	NPC109588
0.9115	High Similarity	NPC475899
0.9107	High Similarity	NPC58448
0.9107	High Similarity	NPC160415
0.9099	High Similarity	NPC258885
0.9099	High Similarity	NPC124296
0.9091	High Similarity	NPC179434
0.9091	High Similarity	NPC31839
0.9091	High Similarity	NPC164419
0.906	High Similarity	NPC469947
0.906	High Similarity	NPC475368
0.906	High Similarity	NPC284449
0.906	High Similarity	NPC470218
0.906	High Similarity	NPC181066
0.9043	High Similarity	NPC301449
0.9043	High Similarity	NPC86222
0.9043	High Similarity	NPC222580
0.9043	High Similarity	NPC171544
0.9043	High Similarity	NPC223301
0.9043	High Similarity	NPC114484
0.9043	High Similarity	NPC477463
0.9043	High Similarity	NPC187618
0.9043	High Similarity	NPC62725
0.9043	High Similarity	NPC297263
0.9043	High Similarity	NPC22956
0.9043	High Similarity	NPC31838
0.9043	High Similarity	NPC104372
0.9043	High Similarity	NPC64715
0.9043	High Similarity	NPC159309
0.9043	High Similarity	NPC11242
0.9043	High Similarity	NPC302887
0.9035	High Similarity	NPC473401
0.9027	High Similarity	NPC471547
0.9009	High Similarity	NPC128925
0.9009	High Similarity	NPC256798
0.9009	High Similarity	NPC116794

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 NPC470514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	2198
0.2-0.3	3903
0.3-0.4	1833
0.4-0.5	533
0.5-0.6	282
0.6-0.7	111
0.7-0.8	29
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD8328	Phase 3
0.8571	High Similarity	NPD8132	Clinical (unspecified phase)
0.8534	High Similarity	NPD8295	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD8133	Approved
0.7913	Intermediate Similarity	NPD6412	Phase 2
0.7661	Intermediate Similarity	NPD8517	Approved
0.7661	Intermediate Similarity	NPD8515	Approved
0.7661	Intermediate Similarity	NPD8516	Approved
0.7522	Intermediate Similarity	NPD7902	Approved
0.752	Intermediate Similarity	NPD8513	Phase 3
0.7442	Intermediate Similarity	NPD7736	Approved
0.744	Intermediate Similarity	NPD8294	Approved
0.744	Intermediate Similarity	NPD8377	Approved
0.7411	Intermediate Similarity	NPD7748	Approved
0.7395	Intermediate Similarity	NPD6686	Approved
0.7385	Intermediate Similarity	NPD7319	Approved
0.7381	Intermediate Similarity	NPD8379	Approved
0.7381	Intermediate Similarity	NPD8335	Approved
0.7381	Intermediate Similarity	NPD8378	Approved
0.7381	Intermediate Similarity	NPD8380	Approved
0.7381	Intermediate Similarity	NPD8296	Approved
0.7323	Intermediate Similarity	NPD6370	Approved
0.7288	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7507	Approved
0.7257	Intermediate Similarity	NPD7900	Approved
0.7257	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD8033	Approved
0.7232	Intermediate Similarity	NPD7515	Phase 2
0.7231	Intermediate Similarity	NPD8293	Discontinued
0.7165	Intermediate Similarity	NPD6059	Approved
0.7165	Intermediate Similarity	NPD6054	Approved
0.7107	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7516	Approved
0.7073	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD7328	Approved
0.7008	Intermediate Similarity	NPD7327	Approved
0.6977	Remote Similarity	NPD6016	Approved
0.6977	Remote Similarity	NPD6015	Approved
0.6947	Remote Similarity	NPD7492	Approved
0.6923	Remote Similarity	NPD5988	Approved
0.6899	Remote Similarity	NPD6319	Approved
0.6894	Remote Similarity	NPD6616	Approved
0.687	Remote Similarity	NPD6067	Discontinued
0.6846	Remote Similarity	NPD7503	Approved
0.6842	Remote Similarity	NPD7078	Approved
0.6797	Remote Similarity	NPD7115	Discovery
0.6783	Remote Similarity	NPD8035	Phase 2
0.6783	Remote Similarity	NPD8034	Phase 2
0.6759	Remote Similarity	NPD7645	Phase 2
0.6746	Remote Similarity	NPD8297	Approved
0.6746	Remote Similarity	NPD6882	Approved
0.6724	Remote Similarity	NPD8171	Discontinued
0.6724	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.664	Remote Similarity	NPD6372	Approved
0.664	Remote Similarity	NPD6373	Approved
0.664	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD3618	Phase 1
0.6593	Remote Similarity	NPD8074	Phase 3
0.6591	Remote Similarity	NPD6921	Approved
0.6587	Remote Similarity	NPD4634	Approved
0.6587	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7638	Approved
0.6562	Remote Similarity	NPD4632	Approved
0.6547	Remote Similarity	NPD8450	Suspended
0.6535	Remote Similarity	NPD6650	Approved
0.6535	Remote Similarity	NPD6649	Approved
0.6532	Remote Similarity	NPD6402	Approved
0.6532	Remote Similarity	NPD5739	Approved
0.6532	Remote Similarity	NPD7128	Approved
0.6532	Remote Similarity	NPD6675	Approved
0.6529	Remote Similarity	NPD7640	Approved
0.6529	Remote Similarity	NPD7639	Approved
0.6496	Remote Similarity	NPD6411	Approved
0.6475	Remote Similarity	NPD8449	Approved
0.6466	Remote Similarity	NPD5328	Approved
0.646	Remote Similarity	NPD4786	Approved
0.6446	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD3667	Approved
0.6429	Remote Similarity	NPD6899	Approved
0.6406	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4755	Approved
0.6356	Remote Similarity	NPD6079	Approved
0.6349	Remote Similarity	NPD5697	Approved
0.6349	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5701	Approved
0.6328	Remote Similarity	NPD6883	Approved
0.6328	Remote Similarity	NPD7290	Approved
0.6328	Remote Similarity	NPD7102	Approved
0.6325	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6101	Approved
0.6303	Remote Similarity	NPD4202	Approved
0.6281	Remote Similarity	NPD4697	Phase 3
0.6279	Remote Similarity	NPD6869	Approved
0.6279	Remote Similarity	NPD6847	Approved
0.6279	Remote Similarity	NPD6617	Approved
0.627	Remote Similarity	NPD6008	Approved
0.626	Remote Similarity	NPD5285	Approved
0.626	Remote Similarity	NPD4696	Approved
0.626	Remote Similarity	NPD5286	Approved
0.626	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6013	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD7604	Phase 2
0.6239	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6084	Phase 2
0.623	Remote Similarity	NPD6083	Phase 2
0.6222	Remote Similarity	NPD5983	Phase 2
0.6218	Remote Similarity	NPD7983	Approved
0.6214	Remote Similarity	NPD5956	Approved
0.6207	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD8337	Approved
0.6187	Remote Similarity	NPD8336	Approved
0.6174	Remote Similarity	NPD3133	Approved
0.6174	Remote Similarity	NPD3665	Phase 1
0.6174	Remote Similarity	NPD3666	Approved
0.6172	Remote Similarity	NPD6011	Approved
0.6167	Remote Similarity	NPD5779	Approved
0.6167	Remote Similarity	NPD5778	Approved
0.616	Remote Similarity	NPD5211	Phase 2
0.616	Remote Similarity	NPD5225	Approved
0.616	Remote Similarity	NPD4633	Approved
0.616	Remote Similarity	NPD5224	Approved
0.616	Remote Similarity	NPD5226	Approved
0.6159	Remote Similarity	NPD6336	Discontinued
0.6154	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3573	Approved
0.6148	Remote Similarity	NPD5222	Approved
0.6148	Remote Similarity	NPD5221	Approved
0.6148	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD4768	Approved
0.6142	Remote Similarity	NPD4767	Approved
0.6134	Remote Similarity	NPD46	Approved
0.6134	Remote Similarity	NPD6698	Approved
0.6127	Remote Similarity	NPD8338	Approved
0.6116	Remote Similarity	NPD5282	Discontinued
0.6115	Remote Similarity	NPD8448	Approved
0.6111	Remote Similarity	NPD5174	Approved
0.6111	Remote Similarity	NPD5175	Approved
0.6106	Remote Similarity	NPD7525	Registered
0.6099	Remote Similarity	NPD8392	Approved
0.6099	Remote Similarity	NPD8391	Approved
0.6099	Remote Similarity	NPD8390	Approved
0.6098	Remote Similarity	NPD5173	Approved
0.6087	Remote Similarity	NPD8299	Approved
0.6087	Remote Similarity	NPD8341	Approved
0.6087	Remote Similarity	NPD8340	Approved
0.6087	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8342	Approved
0.6087	Remote Similarity	NPD3669	Approved
0.608	Remote Similarity	NPD5223	Approved
0.6068	Remote Similarity	NPD7146	Approved
0.6068	Remote Similarity	NPD5330	Approved
0.6068	Remote Similarity	NPD7521	Approved
0.6068	Remote Similarity	NPD6409	Approved
0.6068	Remote Similarity	NPD6684	Approved
0.6068	Remote Similarity	NPD7334	Approved
0.6063	Remote Similarity	NPD5141	Approved
0.605	Remote Similarity	NPD4753	Phase 2
0.605	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5696	Approved
0.6047	Remote Similarity	NPD4729	Approved
0.6047	Remote Similarity	NPD4730	Approved
0.6045	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD8451	Approved
0.6034	Remote Similarity	NPD3668	Phase 3
0.6032	Remote Similarity	NPD7632	Discontinued
0.6026	Remote Similarity	NPD7625	Phase 1
0.6	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD6914	Discontinued
0.5985	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD8444	Approved
0.5984	Remote Similarity	NPD4754	Approved
0.597	Remote Similarity	NPD6940	Discontinued
0.597	Remote Similarity	NPD6274	Approved
0.5966	Remote Similarity	NPD6903	Approved
0.5966	Remote Similarity	NPD5737	Approved
0.5966	Remote Similarity	NPD6672	Approved
0.5956	Remote Similarity	NPD7101	Approved
0.5956	Remote Similarity	NPD7100	Approved
0.5954	Remote Similarity	NPD5250	Approved
0.5954	Remote Similarity	NPD5248	Approved
0.5954	Remote Similarity	NPD5249	Phase 3
0.5954	Remote Similarity	NPD5247	Approved
0.5954	Remote Similarity	NPD5251	Approved
0.5954	Remote Similarity	NPD6371	Approved
0.5942	Remote Similarity	NPD8080	Discontinued
0.5935	Remote Similarity	NPD4629	Approved
0.5935	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD5210	Approved
0.5935	Remote Similarity	NPD5695	Phase 3
0.5931	Remote Similarity	NPD8415	Approved
0.5923	Remote Similarity	NPD5128	Approved
0.5913	Remote Similarity	NPD1779	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