NPASS Compound

Structure

NPC470515 OpenBabel07101719182D 84 92 0 0 1 0 0 0 0 0999 V2000 7.7104 4.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8537 6.9247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0648 -4.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0755 -4.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0648 2.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0755 2.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7134 -0.9892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8567 1.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8567 0.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7104 5.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8567 -1.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8567 1.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4269 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5701 -0.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7134 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5701 -0.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7134 -2.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2836 6.4301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7134 3.9570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1403 2.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5701 4.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4269 -0.9892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8537 5.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8567 -1.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7134 -1.9785 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1403 5.9355 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8567 4.4516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1403 1.9785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4269 3.9570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7134 0.9892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8567 -0.4946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4269 0.9892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9970 6.4301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8567 5.4409 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9970 1.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2836 4.4516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8537 5.9355 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 5.9355 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9970 0.4946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8537 4.9462 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8567 5.4409 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1403 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1403 2.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1403 3.9570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4269 -2.9677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4269 -1.9785 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9970 5.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9970 4.4516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8567 4.4516 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2836 0.4946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2836 2.4731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5701 -3.4624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5701 1.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7134 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8567 -0.4946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5701 -1.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2836 7.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5701 4.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9970 7.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7134 5.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8537 1.9785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2836 5.4409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7104 6.4301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.9247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8537 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7104 4.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7134 5.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1403 -0.9892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9970 2.4731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2836 -3.4624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2836 -1.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1403 5.9355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9970 3.4624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7134 3.9570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4269 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1403 4.9462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.9570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2836 1.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4269 2.9677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2836 1.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9970 4.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 25 1 0 0 0 0 3 54 1 0 0 0 0 4 54 1 0 0 0 0 5 55 1 0 0 0 0 6 55 1 0 0 0 0 8 57 1 0 0 0 0 10 25 2 0 0 0 0 11 12 1 0 0 0 0 11 26 2 0 0 0 0 12 33 1 0 0 0 0 13 16 1 0 0 0 0 13 32 1 0 0 0 0 14 15 1 0 0 0 0 14 34 1 0 0 0 0 15 56 1 0 0 0 0 16 58 1 0 0 0 0 17 18 1 0 0 0 0 17 57 1 0 0 0 0 18 59 1 0 0 0 0 19 27 1 0 0 0 0 19 54 1 0 0 0 0 20 60 1 0 0 0 0 21 61 1 0 0 0 0 22 76 1 0 0 0 0 23 77 1 0 0 0 0 24 78 1 0 0 0 0 25 49 1 0 0 0 0 26 27 1 0 0 0 0 26 57 1 0 0 0 0 27 59 1 6 0 0 0 28 20 1 1 0 0 0 28 35 1 0 0 0 0 28 79 1 0 0 0 0 29 21 1 6 0 0 0 29 36 1 0 0 0 0 29 80 1 0 0 0 0 30 22 1 1 0 0 0 30 37 1 0 0 0 0 30 81 1 0 0 0 0 31 23 1 6 0 0 0 31 38 1 0 0 0 0 31 82 1 0 0 0 0 32 55 1 0 0 0 0 32 56 1 1 0 0 0 33 56 1 1 0 0 0 33 58 1 0 0 0 0 34 55 1 0 0 0 0 34 83 1 1 0 0 0 35 39 1 0 0 0 0 35 62 1 6 0 0 0 36 40 1 0 0 0 0 36 63 1 1 0 0 0 37 41 1 0 0 0 0 37 64 1 6 0 0 0 38 46 1 0 0 0 0 38 65 1 1 0 0 0 39 42 1 0 0 0 0 39 66 1 1 0 0 0 40 43 1 0 0 0 0 40 67 1 6 0 0 0 41 44 1 0 0 0 0 41 68 1 1 0 0 0 42 50 1 0 0 0 0 42 69 1 6 0 0 0 43 51 1 0 0 0 0 43 70 1 1 0 0 0 44 52 1 0 0 0 0 44 71 1 6 0 0 0 45 46 1 0 0 0 0 45 53 1 0 0 0 0 45 72 1 1 0 0 0 46 84 1 6 0 0 0 47 48 1 0 0 0 0 47 54 1 0 0 0 0 47 73 1 1 0 0 0 48 59 1 6 0 0 0 48 74 1 0 0 0 0 49 75 2 0 0 0 0 49 84 1 0 0 0 0 50 76 1 1 0 0 0 50 79 1 0 0 0 0 51 77 1 6 0 0 0 51 80 1 0 0 0 0 52 78 1 1 0 0 0 52 81 1 0 0 0 0 53 82 1 0 0 0 0 53 83 1 6 0 0 0 56 7 1 1 0 0 0 57 58 1 1 0 0 0 58 9 1 1 0 0 0 59 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1204.62
Volume:	1163.858
LogP:	2.108
LogD:	1.602
LogS:	-2.531
# Rotatable Bonds:	16
TPSA:	403.59
# H-Bond Aceptor:	25
# H-Bond Donor:	15
# Rings:	9
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.036
Synthetic Accessibility Score:	7.247
Fsp3:	0.915
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:	-6.128
MDCK Permeability:	0.00019128654093947262
Pgp-inhibitor:	0.208
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	63.62425994873047%
Volume Distribution (VD):	-0.388
Pgp-substrate:	13.39316177368164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	-0.133
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.198
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.194
Carcinogencity:	0.006
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.227

Download Data

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

Natural Product: NPC470515

Natural Product ID:	NPC470515
*Common Name:**	Sorbifoliaside D
IUPAC Name:	[(2R,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8aR,9R,10R,12aS,14aR,14bR)-9,10-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(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]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:	sorbifoliaside D
Standard InCHIKey:	XSQQDTHJAQSLQB-QJPROXSFSA-N
Standard InCHI:	InChI=1S/C59H96O25/c1-10-25(2)49(75)84-46-38(65)31(23-77-51-43(70)40(67)36(63)29(21-61)80-51)82-53(45(46)72)83-34-14-15-56(7)32(55(34,5)6)13-16-58(9)33(56)12-11-26-27-19-54(3,4)47(73)48(74)59(27,18-17-57(26,58)8)24-78-52-44(71)41(68)37(64)30(81-52)22-76-50-42(69)39(66)35(62)28(20-60)79-50/h10-11,27-48,50-53,60-74H,12-24H2,1-9H3/b25-10-/t27-,28+,29+,30+,31+,32-,33+,34-,35+,36+,37+,38+,39-,40-,41-,42+,43+,44+,45+,46-,47-,48-,50+,51+,52+,53-,56-,57+,58+,59-/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC[C@]34CC[C@@]5(C(=CC[C@H]6[C@@]5(C)CC[C@@H]5[C@]6(C)CC[C@@H](C5(C)C)O[C@@H]5O[C@H](CO[C@@H]6O[C@H](CO)[C@H]([C@@H]([C@H]6O)O)O)[C@H]([C@@H]([C@H]5O)OC(=O)/C(=CC)/C)O)[C@@H]4CC([C@H]([C@@H]3O)O)(C)C)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:	CHEMBL2058430
PubChem CID:	66552777
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
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[534455]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	100000.0	nM	PMID[534455]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[534455]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[534455]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[534455]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[534455]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[534455]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	100000.0	nM	PMID[534455]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[534455]

☑ 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 NPC470515 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	270
0.1-0.2	1784
0.2-0.3	4931
0.3-0.4	10220
0.4-0.5	11577
0.5-0.6	6951
0.6-0.7	4115
0.7-0.8	1793
0.8-0.85	520
0.85-0.9	434
0.9-0.95	97
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC470911
0.9908	High Similarity	NPC470915
0.9908	High Similarity	NPC470517
0.955	High Similarity	NPC470914
0.931	High Similarity	NPC470516
0.9286	High Similarity	NPC471548
0.9224	High Similarity	NPC297950
0.9196	High Similarity	NPC473405
0.9123	High Similarity	NPC135369
0.9099	High Similarity	NPC473159
0.9076	High Similarity	NPC476775
0.9076	High Similarity	NPC476774
0.9076	High Similarity	NPC271610
0.9076	High Similarity	NPC476780
0.9074	High Similarity	NPC281939
0.9068	High Similarity	NPC45606
0.9068	High Similarity	NPC220838
0.9068	High Similarity	NPC472269
0.9068	High Similarity	NPC23020
0.9068	High Similarity	NPC472268
0.9068	High Similarity	NPC112492
0.9068	High Similarity	NPC472270
0.9027	High Similarity	NPC471547
0.9	High Similarity	NPC312650
0.9	High Similarity	NPC476776
0.9	High Similarity	NPC277212
0.9	High Similarity	NPC46823
0.9	High Similarity	NPC192765
0.9	High Similarity	NPC30279
0.9	High Similarity	NPC71391
0.9	High Similarity	NPC178264
0.9	High Similarity	NPC473918
0.8992	High Similarity	NPC11577
0.8992	High Similarity	NPC252657
0.8992	High Similarity	NPC305793
0.8992	High Similarity	NPC1314
0.8992	High Similarity	NPC472267
0.8992	High Similarity	NPC273878
0.8992	High Similarity	NPC252289
0.8992	High Similarity	NPC265841
0.8992	High Similarity	NPC88311
0.8992	High Similarity	NPC47995
0.8992	High Similarity	NPC9470
0.8992	High Similarity	NPC107536
0.8992	High Similarity	NPC97918
0.8992	High Similarity	NPC82380
0.8992	High Similarity	NPC244296
0.8992	High Similarity	NPC269484
0.8992	High Similarity	NPC470518
0.8992	High Similarity	NPC141600
0.8992	High Similarity	NPC115656
0.8992	High Similarity	NPC280029
0.8991	High Similarity	NPC475263
0.8929	High Similarity	NPC163183
0.8929	High Similarity	NPC241909
0.8929	High Similarity	NPC151543
0.8929	High Similarity	NPC174720
0.8929	High Similarity	NPC219180
0.8929	High Similarity	NPC96641
0.8929	High Similarity	NPC309714
0.8929	High Similarity	NPC251263
0.8929	High Similarity	NPC155410
0.8929	High Similarity	NPC114287
0.8929	High Similarity	NPC473343
0.8929	High Similarity	NPC473826
0.8929	High Similarity	NPC166422
0.8929	High Similarity	NPC73318
0.8929	High Similarity	NPC295823
0.8929	High Similarity	NPC192600
0.8929	High Similarity	NPC134835
0.8929	High Similarity	NPC46665
0.8929	High Similarity	NPC475287
0.8929	High Similarity	NPC475467
0.8929	High Similarity	NPC323341
0.8929	High Similarity	NPC150400
0.8929	High Similarity	NPC133818
0.8929	High Similarity	NPC114304
0.8926	High Similarity	NPC225791
0.8917	High Similarity	NPC222951
0.8917	High Similarity	NPC43589
0.8917	High Similarity	NPC311178
0.8917	High Similarity	NPC300655
0.8908	High Similarity	NPC477192
0.8908	High Similarity	NPC477191
0.8908	High Similarity	NPC477193
0.8908	High Similarity	NPC477194
0.8899	High Similarity	NPC473586
0.8889	High Similarity	NPC110656
0.8889	High Similarity	NPC203354
0.8889	High Similarity	NPC473127
0.8889	High Similarity	NPC173583
0.8889	High Similarity	NPC148603
0.887	High Similarity	NPC473401
0.8852	High Similarity	NPC476778
0.8852	High Similarity	NPC476777
0.885	High Similarity	NPC161717
0.885	High Similarity	NPC70809
0.885	High Similarity	NPC469782
0.885	High Similarity	NPC100639
0.885	High Similarity	NPC204414
0.885	High Similarity	NPC119592
0.885	High Similarity	NPC476068
0.885	High Similarity	NPC60557
0.885	High Similarity	NPC79643
0.885	High Similarity	NPC123199
0.885	High Similarity	NPC54636
0.885	High Similarity	NPC65105
0.885	High Similarity	NPC43550
0.885	High Similarity	NPC475160
0.885	High Similarity	NPC57484
0.885	High Similarity	NPC473714
0.885	High Similarity	NPC309907
0.885	High Similarity	NPC76972
0.885	High Similarity	NPC305981
0.885	High Similarity	NPC250247
0.885	High Similarity	NPC261506
0.885	High Similarity	NPC71065
0.885	High Similarity	NPC4328
0.885	High Similarity	NPC471550
0.885	High Similarity	NPC293330
0.885	High Similarity	NPC298034
0.885	High Similarity	NPC224381
0.885	High Similarity	NPC41061
0.885	High Similarity	NPC202828
0.885	High Similarity	NPC471385
0.885	High Similarity	NPC227551
0.885	High Similarity	NPC475140
0.885	High Similarity	NPC67857
0.885	High Similarity	NPC294453
0.885	High Similarity	NPC236638
0.8843	High Similarity	NPC475177
0.8843	High Similarity	NPC319719
0.8843	High Similarity	NPC233223
0.8843	High Similarity	NPC322904
0.8843	High Similarity	NPC324933
0.8843	High Similarity	NPC196874
0.8843	High Similarity	NPC475444
0.8843	High Similarity	NPC473679
0.8843	High Similarity	NPC183816
0.8839	High Similarity	NPC292677
0.8839	High Similarity	NPC104400
0.8839	High Similarity	NPC471383
0.8839	High Similarity	NPC475504
0.8839	High Similarity	NPC257468
0.8839	High Similarity	NPC79718
0.8839	High Similarity	NPC101744
0.8839	High Similarity	NPC469946
0.8839	High Similarity	NPC102439
0.8839	High Similarity	NPC104071
0.8839	High Similarity	NPC473373
0.8839	High Similarity	NPC109079
0.8839	High Similarity	NPC10320
0.8839	High Similarity	NPC473383
0.8839	High Similarity	NPC324875
0.8839	High Similarity	NPC139894
0.8839	High Similarity	NPC276093
0.8839	High Similarity	NPC475516
0.8839	High Similarity	NPC139044
0.8833	High Similarity	NPC470913
0.8833	High Similarity	NPC470912
0.8833	High Similarity	NPC477077
0.8833	High Similarity	NPC477196
0.8833	High Similarity	NPC477079
0.8833	High Similarity	NPC477076
0.8807	High Similarity	NPC88349
0.8807	High Similarity	NPC173859
0.8807	High Similarity	NPC470512
0.8803	High Similarity	NPC474423
0.8803	High Similarity	NPC74259
0.8796	High Similarity	NPC473123
0.8796	High Similarity	NPC123796
0.8796	High Similarity	NPC473124
0.8793	High Similarity	NPC476150
0.8793	High Similarity	NPC476127
0.8783	High Similarity	NPC475899
0.8783	High Similarity	NPC237191
0.878	High Similarity	NPC279915
0.878	High Similarity	NPC110700
0.8772	High Similarity	NPC476992
0.8772	High Similarity	NPC288205
0.8772	High Similarity	NPC161674
0.8772	High Similarity	NPC26626
0.8772	High Similarity	NPC51465
0.8772	High Similarity	NPC471384
0.8772	High Similarity	NPC75287
0.8772	High Similarity	NPC305267
0.877	High Similarity	NPC476779
0.8761	High Similarity	NPC258885
0.8761	High Similarity	NPC473128
0.8761	High Similarity	NPC124296
0.8761	High Similarity	NPC40133
0.8761	High Similarity	NPC49413
0.8761	High Similarity	NPC44298
0.8761	High Similarity	NPC290608
0.876	High Similarity	NPC477197
0.876	High Similarity	NPC25998
0.876	High Similarity	NPC478155
0.875	High Similarity	NPC179434
0.875	High Similarity	NPC475281
0.875	High Similarity	NPC477075

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 NPC470515 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	1984
0.2-0.3	3874
0.3-0.4	2075
0.4-0.5	593
0.5-0.6	268
0.6-0.7	73
0.7-0.8	19
0.8-0.85	6
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8632	High Similarity	NPD8294	Approved
0.8632	High Similarity	NPD8377	Approved
0.8559	High Similarity	NPD8296	Approved
0.8559	High Similarity	NPD8335	Approved
0.8559	High Similarity	NPD8380	Approved
0.8559	High Similarity	NPD8379	Approved
0.8559	High Similarity	NPD8378	Approved
0.8403	Intermediate Similarity	NPD8033	Approved
0.8264	Intermediate Similarity	NPD8328	Phase 3
0.8235	Intermediate Similarity	NPD7516	Approved
0.8158	Intermediate Similarity	NPD6686	Approved
0.8151	Intermediate Similarity	NPD7328	Approved
0.8151	Intermediate Similarity	NPD7327	Approved
0.812	Intermediate Similarity	NPD8133	Approved
0.8099	Intermediate Similarity	NPD7503	Approved
0.7931	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7507	Approved
0.7769	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7319	Approved
0.752	Intermediate Similarity	NPD8516	Approved
0.752	Intermediate Similarity	NPD8515	Approved
0.752	Intermediate Similarity	NPD8517	Approved
0.7458	Intermediate Similarity	NPD6412	Phase 2
0.7456	Intermediate Similarity	NPD7638	Approved
0.7391	Intermediate Similarity	NPD7640	Approved
0.7391	Intermediate Similarity	NPD7639	Approved
0.7381	Intermediate Similarity	NPD8513	Phase 3
0.7257	Intermediate Similarity	NPD7748	Approved
0.7217	Intermediate Similarity	NPD7902	Approved
0.719	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7736	Approved
0.7155	Intermediate Similarity	NPD4225	Approved
0.708	Intermediate Similarity	NPD7515	Phase 2
0.7073	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5344	Discontinued
0.7009	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7900	Approved
0.6957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7115	Discovery
0.6923	Remote Similarity	NPD7625	Phase 1
0.6842	Remote Similarity	NPD8293	Discontinued
0.6842	Remote Similarity	NPD7838	Discovery
0.6833	Remote Similarity	NPD7632	Discontinued
0.6794	Remote Similarity	NPD6370	Approved
0.6759	Remote Similarity	NPD7645	Phase 2
0.6748	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6882	Approved
0.6746	Remote Similarity	NPD8297	Approved
0.6724	Remote Similarity	NPD8171	Discontinued
0.6696	Remote Similarity	NPD46	Approved
0.6696	Remote Similarity	NPD6698	Approved
0.6694	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6642	Remote Similarity	NPD6616	Approved
0.6641	Remote Similarity	NPD6319	Approved
0.6641	Remote Similarity	NPD6054	Approved
0.6593	Remote Similarity	NPD7078	Approved
0.6585	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4632	Approved
0.6547	Remote Similarity	NPD8450	Suspended
0.6515	Remote Similarity	NPD6059	Approved
0.6493	Remote Similarity	NPD6067	Discontinued
0.6475	Remote Similarity	NPD8449	Approved
0.6471	Remote Similarity	NPD8074	Phase 3
0.6466	Remote Similarity	NPD6016	Approved
0.6466	Remote Similarity	NPD6015	Approved
0.646	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD6881	Approved
0.6418	Remote Similarity	NPD5988	Approved
0.6406	Remote Similarity	NPD8130	Phase 1
0.6406	Remote Similarity	NPD6649	Approved
0.6406	Remote Similarity	NPD6650	Approved
0.64	Remote Similarity	NPD5739	Approved
0.64	Remote Similarity	NPD6402	Approved
0.64	Remote Similarity	NPD7128	Approved
0.64	Remote Similarity	NPD6675	Approved
0.6378	Remote Similarity	NPD6373	Approved
0.6378	Remote Similarity	NPD6372	Approved
0.6356	Remote Similarity	NPD8035	Phase 2
0.6356	Remote Similarity	NPD8034	Phase 2
0.6349	Remote Similarity	NPD5697	Approved
0.6328	Remote Similarity	NPD6883	Approved
0.6328	Remote Similarity	NPD7290	Approved
0.6328	Remote Similarity	NPD7102	Approved
0.6299	Remote Similarity	NPD7320	Approved
0.6279	Remote Similarity	NPD6847	Approved
0.6279	Remote Similarity	NPD6617	Approved
0.6279	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6222	Remote Similarity	NPD5983	Phase 2
0.6222	Remote Similarity	NPD6921	Approved
0.622	Remote Similarity	NPD5701	Approved
0.6172	Remote Similarity	NPD6011	Approved
0.6167	Remote Similarity	NPD6399	Phase 3
0.6159	Remote Similarity	NPD6336	Discontinued
0.6154	Remote Similarity	NPD3573	Approved
0.614	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD6053	Discontinued
0.6106	Remote Similarity	NPD7525	Registered
0.6102	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6084	Phase 2
0.6098	Remote Similarity	NPD6083	Phase 2
0.6094	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3669	Approved
0.6087	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6079	Approved
0.6077	Remote Similarity	NPD6371	Approved
0.6077	Remote Similarity	NPD4634	Approved
0.6071	Remote Similarity	NPD6033	Approved
0.6068	Remote Similarity	NPD3618	Phase 1
0.6056	Remote Similarity	NPD7260	Phase 2
0.605	Remote Similarity	NPD6051	Approved
0.605	Remote Similarity	NPD5328	Approved
0.604	Remote Similarity	NPD7266	Discontinued
0.6032	Remote Similarity	NPD5211	Phase 2
0.6031	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD7524	Approved
0.6016	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4696	Approved
0.5986	Remote Similarity	NPD8390	Approved
0.5986	Remote Similarity	NPD8392	Approved
0.5986	Remote Similarity	NPD8391	Approved
0.5983	Remote Similarity	NPD1694	Approved
0.597	Remote Similarity	NPD6274	Approved
0.5968	Remote Similarity	NPD4755	Approved
0.5964	Remote Similarity	NPD7799	Discontinued
0.5957	Remote Similarity	NPD8337	Approved
0.5957	Remote Similarity	NPD8336	Approved
0.5956	Remote Similarity	NPD7101	Approved
0.5956	Remote Similarity	NPD7100	Approved
0.595	Remote Similarity	NPD7637	Suspended
0.595	Remote Similarity	NPD7983	Approved
0.595	Remote Similarity	NPD6411	Approved
0.5938	Remote Similarity	NPD5141	Approved
0.5932	Remote Similarity	NPD7146	Approved
0.5932	Remote Similarity	NPD7521	Approved
0.5932	Remote Similarity	NPD6409	Approved
0.5932	Remote Similarity	NPD6684	Approved
0.5932	Remote Similarity	NPD5330	Approved
0.5932	Remote Similarity	NPD7334	Approved
0.5929	Remote Similarity	NPD8451	Approved
0.5917	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD4633	Approved
0.5906	Remote Similarity	NPD5224	Approved
0.5906	Remote Similarity	NPD5225	Approved
0.5906	Remote Similarity	NPD5226	Approved
0.5903	Remote Similarity	NPD8338	Approved
0.5902	Remote Similarity	NPD5778	Approved
0.5902	Remote Similarity	NPD4202	Approved
0.5902	Remote Similarity	NPD5779	Approved
0.589	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5221	Approved
0.5887	Remote Similarity	NPD5222	Approved
0.5882	Remote Similarity	NPD6335	Approved
0.5875	Remote Similarity	NPD8455	Phase 2
0.5873	Remote Similarity	NPD4700	Approved
0.587	Remote Similarity	NPD8444	Approved
0.5859	Remote Similarity	NPD5174	Approved
0.5859	Remote Similarity	NPD5175	Approved
0.5852	Remote Similarity	NPD6868	Approved
0.585	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD8312	Approved
0.5848	Remote Similarity	NPD8313	Approved
0.584	Remote Similarity	NPD5173	Approved
0.5833	Remote Similarity	NPD5737	Approved
0.5833	Remote Similarity	NPD6903	Approved
0.5833	Remote Similarity	NPD6672	Approved
0.5827	Remote Similarity	NPD4159	Approved
0.5827	Remote Similarity	NPD5223	Approved
0.5822	Remote Similarity	NPD8415	Approved
0.5809	Remote Similarity	NPD6317	Approved
0.5806	Remote Similarity	NPD5695	Phase 3
0.5802	Remote Similarity	NPD4730	Approved
0.5802	Remote Similarity	NPD4729	Approved
0.5794	Remote Similarity	NPD5696	Approved
0.5793	Remote Similarity	NPD6845	Suspended
0.5786	Remote Similarity	NPD7642	Approved
0.5785	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6101	Approved
0.5774	Remote Similarity	NPD7228	Approved
0.5769	Remote Similarity	NPD4767	Approved
0.5769	Remote Similarity	NPD4768	Approved
0.5766	Remote Similarity	NPD6314	Approved
0.5766	Remote Similarity	NPD7641	Discontinued
0.5766	Remote Similarity	NPD6313	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