NPASS Compound

Structure

CID278419 OpenBabel06191716082D 37 40 0 0 1 0 0 0 0 0999 V2000 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 4 34 1 0 0 0 0 5 10 1 0 0 0 0 5 12 2 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 13 3 1 1 0 0 0 13 20 1 0 0 0 0 13 35 1 0 0 0 0 14 24 1 0 0 0 0 15 34 1 0 0 0 0 16 17 1 0 0 0 0 16 25 2 0 0 0 0 17 28 1 0 0 0 0 18 19 2 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 25 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 6 0 0 0 21 26 1 0 0 0 0 21 31 2 0 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 27 1 0 0 0 0 23 33 1 1 0 0 0 24 26 2 0 0 0 0 24 36 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 35 1 0 0 0 0 27 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.18
Volume:	505.496
LogP:	4.145
LogD:	2.302
LogS:	-3.968
# Rotatable Bonds:	6
TPSA:	159.05
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	4.143
Fsp3:	0.37
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.724
MDCK Permeability:	1.0548576028668322e-05
Pgp-inhibitor:	0.588
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.139
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.804

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	83.1944808959961%
Volume Distribution (VD):	0.873
Pgp-substrate:	14.449527740478516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.366
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.157
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.726
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.532
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.175
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	4.9
Half-life (T1/2):	0.435

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.799
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.787
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.437
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.184

Download Data

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

Natural Product: NPC278419

Natural Product ID:	NPC278419
*Common Name:**	7-Hydroxy-3-O-L-Rhamnose-8-Prenyl-4'-Methoxy Chrysin
IUPAC Name:	5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	NGMYNFJANBHLKA-LVKFHIPRSA-N
Standard InCHI:	InChI=1S/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1
SMILES:	COc1ccc(cc1)c1oc2c(CC=C(C)C)c(O)cc(c2c(=O)c1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560116
PubChem CID:	5488822
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2007.07.001]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	root	n.a.	n.a.	PMID[15921428]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24066589]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO31054	Epimedium brevicornum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29338226]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8699184]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31054	Epimedium brevicornum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31054	Epimedium brevicornum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12602	Leuzea centauroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO940	Vernonia anisochaetoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26095	Hypericum revolutum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12828	Dysidea tupha	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4759	Helleborus multifidus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8609	Hopea utilis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5534	Alternaria kikuchiana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10970	Osmorhiza aristata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8129	Inocybe geophylla	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1695	Monascus pilosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10010	Evernia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7874	Helichrysum lepidissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4322	Scabiosa succisa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6861	Galium dasypodum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12118	Cleistopholis staudtii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO218	Acer carpinifolium	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11339	Litsea salicifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11506	Stipa vaseyi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	3
Others	3

Activity Type	# Activity
Individual Protein	1
Others	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT273	Individual Protein	Phosphodiesterase 5A	Homo sapiens	IC50	=	1700.0	nM	PMID[543427]
NPT21762	SINGLE PROTEIN	Lysine-specific histone demethylase 1	Homo sapiens	IC50	=	16700.0	nM	PMID[543426]
NPT2	Others	Unspecified		Ratio IC50	=	1.28	n.a.	PMID[19523827]
NPT2	Others	Unspecified		Ratio IC50	=	1.39	n.a.	PMID[19523827]
NPT2	Others	Unspecified		Ratio IC50	=	1.61	n.a.	PMID[19523827]
NPT2	Others	Unspecified		IC50	>	100000	nM	PMID[19523827]

☑ 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 NPC278419 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	427
0.1-0.2	1672
0.2-0.3	3768
0.3-0.4	9054
0.4-0.5	9198
0.5-0.6	4601
0.6-0.7	5540
0.7-0.8	4673
0.8-0.85	2361
0.85-0.9	869
0.9-0.95	477
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC66087
1.0	High Similarity	NPC179198
0.9935	High Similarity	NPC131745
0.9871	High Similarity	NPC183672
0.9806	High Similarity	NPC259834
0.9747	High Similarity	NPC5319
0.974	High Similarity	NPC111929
0.974	High Similarity	NPC320283
0.974	High Similarity	NPC41121
0.974	High Similarity	NPC472459
0.9679	High Similarity	NPC44947
0.9677	High Similarity	NPC153342
0.9675	High Similarity	NPC133671
0.9675	High Similarity	NPC108831
0.9675	High Similarity	NPC182634
0.9675	High Similarity	NPC77672
0.9675	High Similarity	NPC54802
0.9675	High Similarity	NPC135391
0.9675	High Similarity	NPC197304
0.9675	High Similarity	NPC78263
0.9618	High Similarity	NPC257566
0.9618	High Similarity	NPC124155
0.9615	High Similarity	NPC173582
0.9615	High Similarity	NPC215710
0.9615	High Similarity	NPC473438
0.9615	High Similarity	NPC159579
0.9615	High Similarity	NPC47923
0.9615	High Similarity	NPC163242
0.9615	High Similarity	NPC129217
0.9615	High Similarity	NPC265885
0.9615	High Similarity	NPC249281
0.9615	High Similarity	NPC476215
0.9615	High Similarity	NPC85707
0.9615	High Similarity	NPC253788
0.9615	High Similarity	NPC224530
0.9615	High Similarity	NPC139320
0.9615	High Similarity	NPC48093
0.9615	High Similarity	NPC216496
0.9615	High Similarity	NPC246943
0.9615	High Similarity	NPC116458
0.9615	High Similarity	NPC259957
0.9615	High Similarity	NPC181465
0.9615	High Similarity	NPC276377
0.9613	High Similarity	NPC73511
0.961	High Similarity	NPC307938
0.961	High Similarity	NPC203500
0.961	High Similarity	NPC323593
0.9554	High Similarity	NPC240306
0.9554	High Similarity	NPC150164
0.9554	High Similarity	NPC27942
0.9551	High Similarity	NPC187379
0.9551	High Similarity	NPC471079
0.9551	High Similarity	NPC470405
0.9551	High Similarity	NPC304741
0.9551	High Similarity	NPC472320
0.9548	High Similarity	NPC156457
0.9548	High Similarity	NPC313163
0.9548	High Similarity	NPC258035
0.9548	High Similarity	NPC197896
0.9548	High Similarity	NPC161749
0.9548	High Similarity	NPC23817
0.9548	High Similarity	NPC6985
0.9545	High Similarity	NPC470603
0.9545	High Similarity	NPC95090
0.9545	High Similarity	NPC470604
0.9545	High Similarity	NPC27408
0.9545	High Similarity	NPC304745
0.9545	High Similarity	NPC111341
0.9545	High Similarity	NPC470605
0.9506	High Similarity	NPC294629
0.9494	High Similarity	NPC121703
0.949	High Similarity	NPC297987
0.949	High Similarity	NPC170052
0.949	High Similarity	NPC303913
0.949	High Similarity	NPC64305
0.949	High Similarity	NPC470125
0.949	High Similarity	NPC282169
0.949	High Similarity	NPC135846
0.9487	High Similarity	NPC104677
0.9484	High Similarity	NPC206378
0.9484	High Similarity	NPC45165
0.9481	High Similarity	NPC108706
0.9481	High Similarity	NPC78021
0.9481	High Similarity	NPC87304
0.9481	High Similarity	NPC143851
0.9481	High Similarity	NPC211158
0.9481	High Similarity	NPC29763
0.9481	High Similarity	NPC210003
0.9481	High Similarity	NPC106625
0.9481	High Similarity	NPC268193
0.9481	High Similarity	NPC83283
0.9481	High Similarity	NPC268950
0.9481	High Similarity	NPC39360
0.9437	High Similarity	NPC173637
0.9437	High Similarity	NPC127546
0.9437	High Similarity	NPC52550
0.9437	High Similarity	NPC317489
0.9437	High Similarity	NPC84362
0.9437	High Similarity	NPC223424
0.9434	High Similarity	NPC72016
0.943	High Similarity	NPC190450
0.9427	High Similarity	NPC136761
0.9427	High Similarity	NPC306978
0.9423	High Similarity	NPC44931
0.9423	High Similarity	NPC288084
0.9423	High Similarity	NPC129827
0.9423	High Similarity	NPC60966
0.9423	High Similarity	NPC470606
0.9423	High Similarity	NPC65003
0.9423	High Similarity	NPC473512
0.9419	High Similarity	NPC259710
0.9419	High Similarity	NPC99233
0.9419	High Similarity	NPC48579
0.9419	High Similarity	NPC97052
0.9419	High Similarity	NPC304207
0.9419	High Similarity	NPC217706
0.9419	High Similarity	NPC169248
0.9419	High Similarity	NPC26195
0.9419	High Similarity	NPC39351
0.9419	High Similarity	NPC72649
0.9419	High Similarity	NPC207809
0.9416	High Similarity	NPC244583
0.9416	High Similarity	NPC56232
0.9416	High Similarity	NPC150123
0.9416	High Similarity	NPC161881
0.9416	High Similarity	NPC10807
0.9416	High Similarity	NPC121001
0.9416	High Similarity	NPC259182
0.939	High Similarity	NPC168584
0.9379	High Similarity	NPC225434
0.9379	High Similarity	NPC52382
0.9379	High Similarity	NPC120099
0.9379	High Similarity	NPC219904
0.9379	High Similarity	NPC223747
0.9379	High Similarity	NPC203050
0.9379	High Similarity	NPC270578
0.9375	High Similarity	NPC308404
0.9375	High Similarity	NPC221342
0.9375	High Similarity	NPC189564
0.9375	High Similarity	NPC142142
0.9375	High Similarity	NPC276222
0.9375	High Similarity	NPC477613
0.9375	High Similarity	NPC203145
0.9375	High Similarity	NPC145038
0.9375	High Similarity	NPC186816
0.9375	High Similarity	NPC179950
0.9375	High Similarity	NPC476470
0.9375	High Similarity	NPC113968
0.9375	High Similarity	NPC12013
0.9375	High Similarity	NPC118284
0.9375	High Similarity	NPC277174
0.9375	High Similarity	NPC256188
0.9375	High Similarity	NPC73855
0.9375	High Similarity	NPC253662
0.9375	High Similarity	NPC88789
0.9375	High Similarity	NPC56077
0.9375	High Similarity	NPC328940
0.9375	High Similarity	NPC135599
0.9375	High Similarity	NPC281131
0.9375	High Similarity	NPC274618
0.9375	High Similarity	NPC11432
0.9375	High Similarity	NPC64425
0.9375	High Similarity	NPC32641
0.9363	High Similarity	NPC138811
0.9363	High Similarity	NPC308265
0.9363	High Similarity	NPC22062
0.9363	High Similarity	NPC473634
0.9363	High Similarity	NPC43761
0.9363	High Similarity	NPC470607
0.9359	High Similarity	NPC261866
0.9359	High Similarity	NPC127406
0.9359	High Similarity	NPC170475
0.9355	High Similarity	NPC248793
0.9355	High Similarity	NPC236756
0.9355	High Similarity	NPC311579
0.9355	High Similarity	NPC180301
0.9351	High Similarity	NPC319910
0.9351	High Similarity	NPC328740
0.9351	High Similarity	NPC209846
0.9351	High Similarity	NPC262039
0.9351	High Similarity	NPC262038
0.9351	High Similarity	NPC278476
0.9351	High Similarity	NPC477897
0.9351	High Similarity	NPC289774
0.9351	High Similarity	NPC254412
0.9321	High Similarity	NPC78734
0.9321	High Similarity	NPC76047
0.9321	High Similarity	NPC244776
0.9321	High Similarity	NPC206123
0.9321	High Similarity	NPC116864
0.9321	High Similarity	NPC95866
0.9321	High Similarity	NPC150767
0.9317	High Similarity	NPC325555
0.9317	High Similarity	NPC92565
0.9317	High Similarity	NPC226304
0.9317	High Similarity	NPC160156
0.9317	High Similarity	NPC265530
0.9313	High Similarity	NPC129264
0.9313	High Similarity	NPC76831
0.9313	High Similarity	NPC135358

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 NPC278419 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	916
0.2-0.3	1800
0.3-0.4	2676
0.4-0.5	1950
0.5-0.6	963
0.6-0.7	293
0.7-0.8	125
0.8-0.85	26
0.85-0.9	13
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9747	High Similarity	NPD7804	Clinical (unspecified phase)
0.9548	High Similarity	NPD4381	Clinical (unspecified phase)
0.9264	High Similarity	NPD6797	Phase 2
0.9207	High Similarity	NPD7251	Discontinued
0.9177	High Similarity	NPD7075	Discontinued
0.9161	High Similarity	NPD4380	Phase 2
0.9152	High Similarity	NPD7808	Phase 3
0.9045	High Similarity	NPD6801	Discontinued
0.9036	High Similarity	NPD4338	Clinical (unspecified phase)
0.9024	High Similarity	NPD7054	Approved
0.8987	High Similarity	NPD7096	Clinical (unspecified phase)
0.897	High Similarity	NPD7472	Approved
0.897	High Similarity	NPD7074	Phase 3
0.8961	High Similarity	NPD4378	Clinical (unspecified phase)
0.8848	High Similarity	NPD3818	Discontinued
0.875	High Similarity	NPD6559	Discontinued
0.875	High Similarity	NPD2393	Clinical (unspecified phase)
0.8727	High Similarity	NPD6166	Phase 2
0.8727	High Similarity	NPD6168	Clinical (unspecified phase)
0.8727	High Similarity	NPD6167	Clinical (unspecified phase)
0.8608	High Similarity	NPD5403	Approved
0.858	High Similarity	NPD3817	Phase 2
0.858	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD1934	Approved
0.8535	High Similarity	NPD6799	Approved
0.8509	High Similarity	NPD7411	Suspended
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD5401	Approved
0.8466	Intermediate Similarity	NPD5402	Approved
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8409	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8323	Intermediate Similarity	NPD2796	Approved
0.8313	Intermediate Similarity	NPD1512	Approved
0.8303	Intermediate Similarity	NPD3882	Suspended
0.8293	Intermediate Similarity	NPD2801	Approved
0.8293	Intermediate Similarity	NPD7819	Suspended
0.8258	Intermediate Similarity	NPD1510	Phase 2
0.8214	Intermediate Similarity	NPD6959	Discontinued
0.8193	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7584	Approved
0.8047	Intermediate Similarity	NPD5494	Approved
0.8046	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8312	Approved
0.8011	Intermediate Similarity	NPD8313	Approved
0.8	Intermediate Similarity	NPD1240	Approved
0.7989	Intermediate Similarity	NPD6781	Approved
0.7989	Intermediate Similarity	NPD6776	Approved
0.7989	Intermediate Similarity	NPD6782	Approved
0.7989	Intermediate Similarity	NPD6778	Approved
0.7989	Intermediate Similarity	NPD6779	Approved
0.7989	Intermediate Similarity	NPD6780	Approved
0.7989	Intermediate Similarity	NPD6777	Approved
0.7977	Intermediate Similarity	NPD3751	Discontinued
0.7976	Intermediate Similarity	NPD7768	Phase 2
0.7964	Intermediate Similarity	NPD8455	Phase 2
0.7957	Intermediate Similarity	NPD7435	Discontinued
0.7953	Intermediate Similarity	NPD3787	Discontinued
0.7931	Intermediate Similarity	NPD5844	Phase 1
0.7898	Intermediate Similarity	NPD1607	Approved
0.7888	Intermediate Similarity	NPD3750	Approved
0.7888	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6232	Discontinued
0.7826	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7766	Intermediate Similarity	NPD7697	Approved
0.7766	Intermediate Similarity	NPD7698	Approved
0.7766	Intermediate Similarity	NPD7696	Phase 3
0.7725	Intermediate Similarity	NPD7870	Phase 2
0.7725	Intermediate Similarity	NPD7871	Phase 2
0.7719	Intermediate Similarity	NPD3749	Approved
0.7717	Intermediate Similarity	NPD6535	Approved
0.7717	Intermediate Similarity	NPD6534	Approved
0.7716	Intermediate Similarity	NPD2800	Approved
0.7711	Intermediate Similarity	NPD920	Approved
0.7708	Intermediate Similarity	NPD7874	Approved
0.7708	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7585	Approved
0.7696	Intermediate Similarity	NPD7701	Phase 2
0.7688	Intermediate Similarity	NPD1247	Approved
0.7665	Intermediate Similarity	NPD1653	Approved
0.7656	Intermediate Similarity	NPD8151	Discontinued
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7583	Approved
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2935	Discontinued
0.764	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD5953	Discontinued
0.7622	Intermediate Similarity	NPD4360	Phase 2
0.7622	Intermediate Similarity	NPD4363	Phase 3
0.7619	Intermediate Similarity	NPD7458	Discontinued
0.7607	Intermediate Similarity	NPD1243	Approved
0.7605	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7699	Phase 2
0.7594	Intermediate Similarity	NPD7700	Phase 2
0.759	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD2533	Approved
0.759	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2534	Approved
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.7578	Intermediate Similarity	NPD3748	Approved
0.7577	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7783	Phase 2
0.7577	Intermediate Similarity	NPD7801	Approved
0.7576	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7228	Approved
0.7562	Intermediate Similarity	NPD6651	Approved
0.7544	Intermediate Similarity	NPD1465	Phase 2
0.7539	Intermediate Similarity	NPD8320	Phase 1
0.7539	Intermediate Similarity	NPD8319	Approved
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6798	Discontinued
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7528	Intermediate Similarity	NPD7286	Phase 2
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6823	Phase 2
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD37	Approved
0.7471	Intermediate Similarity	NPD6234	Discontinued
0.7469	Intermediate Similarity	NPD7033	Discontinued
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7458	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4967	Phase 2
0.7457	Intermediate Similarity	NPD4966	Approved
0.7457	Intermediate Similarity	NPD4965	Approved
0.7438	Intermediate Similarity	NPD1613	Approved
0.7438	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD4908	Phase 1
0.7403	Intermediate Similarity	NPD1091	Approved
0.7401	Intermediate Similarity	NPD3926	Phase 2
0.7391	Intermediate Similarity	NPD8150	Discontinued
0.7391	Intermediate Similarity	NPD1933	Approved
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7391	Intermediate Similarity	NPD6355	Discontinued
0.7389	Intermediate Similarity	NPD2798	Approved
0.7375	Intermediate Similarity	NPD6233	Phase 2
0.7327	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7390	Discontinued
0.7305	Intermediate Similarity	NPD6190	Approved
0.7296	Intermediate Similarity	NPD6832	Phase 2
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1652	Phase 2
0.7287	Intermediate Similarity	NPD6212	Phase 3
0.7287	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6213	Phase 3
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7229	Intermediate Similarity	NPD2424	Discontinued
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD943	Approved
0.7215	Intermediate Similarity	NPD1203	Approved
0.7213	Intermediate Similarity	NPD7240	Approved
0.7212	Intermediate Similarity	NPD6099	Approved
0.7212	Intermediate Similarity	NPD6100	Approved
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3268	Approved
0.7188	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5049	Phase 3
0.7125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7930	Approved
0.7107	Intermediate Similarity	NPD2797	Approved
0.7101	Intermediate Similarity	NPD3887	Approved
0.7101	Intermediate Similarity	NPD2309	Approved
0.7101	Intermediate Similarity	NPD2354	Approved
0.7091	Intermediate Similarity	NPD7097	Phase 1
0.7086	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7073	Intermediate Similarity	NPD230	Phase 1
0.7072	Intermediate Similarity	NPD2403	Approved
0.707	Intermediate Similarity	NPD422	Phase 1
0.7065	Intermediate Similarity	NPD3823	Discontinued
0.7059	Intermediate Similarity	NPD5058	Phase 3

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