NPASS Compound

Structure

CID270456 OpenBabel06191716072D 22 24 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 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 -3.4641 1.0000 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 0.8660 1.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 -2.5981 1.5000 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 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 15 2 0 0 0 0 11 13 1 1 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	305.051
LogP:	2.761
LogD:	2.989
LogS:	-3.67
# Rotatable Bonds:	3
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.912
Synthetic Accessibility Score:	2.932
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	1.6547770428587683e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.587
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	98.67889404296875%
Volume Distribution (VD):	0.476
Pgp-substrate:	1.928052306175232%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.845
CYP2C19-substrate:	0.656
CYP2C9-inhibitor:	0.684
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.721
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.554
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	11.046
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.384
Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.928
Carcinogencity:	0.597
Eye Corrosion:	0.003
Eye Irritation:	0.829
Respiratory Toxicity:	0.661

Download Data

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

Natural Product: NPC270456

Natural Product ID:	NPC270456
*Common Name:**	(3R)-Mucronulatol
IUPAC Name:	(3R)-3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
Synonyms:	(3R)-Mucronulatol
Standard InCHIKey:	NUNFZNIXYWTZMW-NSHDSACASA-N
Standard InCHI:	InChI=1S/C17H18O5/c1-20-14-6-5-13(17(21-2)16(14)19)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3/t11-/m0/s1
SMILES:	COc1c(ccc(c1O)OC)[C@@H]1COc2c(C1)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087024
PubChem CID:	13873811
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[10661881]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125236]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257536]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO10682	Cystoseira mediterranea	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2045820]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22032651]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30219526]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5457	Dalbergia congestiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10682	Cystoseira mediterranea	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7887	Schultesia guianensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16096	Astragalus adsurgens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10038.1	Abies pinsapo var. marocana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5457	Dalbergia congestiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16182	Desmodium canadense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13641	Napoleonaea vogelii	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13520	Craibiodendron yunnanense	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10947	Aspilia parvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15553	Barringtonia acutangula	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1281	Schleichera trijuga	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15206	Mabea fistulifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10447	Triclisia subcordata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12581	Corydalis densiflora	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29027	Khaya grandifoliola	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[485129]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	6.3	uM	PMID[485129]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	7.8	uM	PMID[485129]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.9	uM	PMID[485129]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	6.4	uM	PMID[485129]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.4	uM	PMID[485129]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[485129]

☑ 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 NPC270456 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	426
0.1-0.2	1639
0.2-0.3	4615
0.3-0.4	12553
0.4-0.5	5428
0.5-0.6	3886
0.6-0.7	6099
0.7-0.8	5858
0.8-0.85	1096
0.85-0.9	676
0.9-0.95	358
0.95-1	63

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC162659
1.0	High Similarity	NPC248727
1.0	High Similarity	NPC265433
0.9847	High Similarity	NPC70682
0.9847	High Similarity	NPC245207
0.9847	High Similarity	NPC260741
0.9847	High Similarity	NPC319647
0.9847	High Similarity	NPC127218
0.9847	High Similarity	NPC25966
0.9845	High Similarity	NPC317380
0.9773	High Similarity	NPC309124
0.9773	High Similarity	NPC184797
0.9771	High Similarity	NPC276490
0.9769	High Similarity	NPC112939
0.9769	High Similarity	NPC94750
0.9769	High Similarity	NPC470356
0.9769	High Similarity	NPC474206
0.9769	High Similarity	NPC121812
0.9769	High Similarity	NPC112246
0.9699	High Similarity	NPC35216
0.9699	High Similarity	NPC471389
0.9697	High Similarity	NPC232164
0.9697	High Similarity	NPC236306
0.9697	High Similarity	NPC473739
0.9695	High Similarity	NPC474639
0.9695	High Similarity	NPC173660
0.9695	High Similarity	NPC16435
0.9695	High Similarity	NPC306441
0.9695	High Similarity	NPC230734
0.9695	High Similarity	NPC227503
0.969	High Similarity	NPC127624
0.969	High Similarity	NPC86655
0.969	High Similarity	NPC202762
0.9627	High Similarity	NPC107161
0.9627	High Similarity	NPC59841
0.9627	High Similarity	NPC2613
0.9627	High Similarity	NPC475891
0.9627	High Similarity	NPC204347
0.9624	High Similarity	NPC259519
0.9621	High Similarity	NPC176051
0.9621	High Similarity	NPC211549
0.9621	High Similarity	NPC102904
0.9621	High Similarity	NPC103976
0.9621	High Similarity	NPC107551
0.9621	High Similarity	NPC326797
0.9621	High Similarity	NPC474282
0.9618	High Similarity	NPC61946
0.9618	High Similarity	NPC151224
0.9618	High Similarity	NPC195022
0.9618	High Similarity	NPC234333
0.9618	High Similarity	NPC260898
0.9618	High Similarity	NPC47398
0.9615	High Similarity	NPC168059
0.9615	High Similarity	NPC11060
0.9615	High Similarity	NPC229442
0.9552	High Similarity	NPC247291
0.9549	High Similarity	NPC471388
0.9545	High Similarity	NPC269091
0.9545	High Similarity	NPC302701
0.9545	High Similarity	NPC234952
0.9542	High Similarity	NPC478085
0.9485	High Similarity	NPC280092
0.9485	High Similarity	NPC93323
0.9485	High Similarity	NPC473108
0.9485	High Similarity	NPC45257
0.9485	High Similarity	NPC12641
0.9478	High Similarity	NPC27495
0.9478	High Similarity	NPC254759
0.9478	High Similarity	NPC160283
0.947	High Similarity	NPC473413
0.947	High Similarity	NPC164787
0.9466	High Similarity	NPC263064
0.9466	High Similarity	NPC475840
0.9412	High Similarity	NPC47633
0.9412	High Similarity	NPC85264
0.9412	High Similarity	NPC102044
0.9407	High Similarity	NPC178054
0.9407	High Similarity	NPC87725
0.9407	High Similarity	NPC263261
0.9403	High Similarity	NPC32630
0.9403	High Similarity	NPC292882
0.9398	High Similarity	NPC470802
0.9398	High Similarity	NPC472336
0.9398	High Similarity	NPC472334
0.9394	High Similarity	NPC106215
0.9394	High Similarity	NPC170694
0.9389	High Similarity	NPC6451
0.9389	High Similarity	NPC15658
0.9389	High Similarity	NPC126029
0.9389	High Similarity	NPC261619
0.9389	High Similarity	NPC253105
0.9389	High Similarity	NPC185604
0.9389	High Similarity	NPC201587
0.9389	High Similarity	NPC61477
0.9389	High Similarity	NPC78770
0.9389	High Similarity	NPC219876
0.9385	High Similarity	NPC91291
0.938	High Similarity	NPC46274
0.938	High Similarity	NPC226331
0.9348	High Similarity	NPC87794
0.9348	High Similarity	NPC211758
0.9343	High Similarity	NPC50250
0.9343	High Similarity	NPC63879
0.9333	High Similarity	NPC266197
0.9333	High Similarity	NPC22317
0.9333	High Similarity	NPC291101
0.9323	High Similarity	NPC472337
0.9318	High Similarity	NPC158331
0.9313	High Similarity	NPC268342
0.9313	High Similarity	NPC220825
0.9313	High Similarity	NPC232275
0.9313	High Similarity	NPC474017
0.9313	High Similarity	NPC12275
0.9313	High Similarity	NPC42760
0.9313	High Similarity	NPC474356
0.9313	High Similarity	NPC268266
0.9313	High Similarity	NPC472597
0.9313	High Similarity	NPC45715
0.9302	High Similarity	NPC324112
0.9302	High Similarity	NPC282000
0.9302	High Similarity	NPC169474
0.9302	High Similarity	NPC210355
0.9302	High Similarity	NPC159968
0.9302	High Similarity	NPC74817
0.9302	High Similarity	NPC250432
0.9302	High Similarity	NPC127587
0.9302	High Similarity	NPC293054
0.9302	High Similarity	NPC246620
0.9302	High Similarity	NPC5447
0.9302	High Similarity	NPC82679
0.9302	High Similarity	NPC124452
0.9302	High Similarity	NPC236791
0.9281	High Similarity	NPC21776
0.9281	High Similarity	NPC16269
0.9275	High Similarity	NPC307466
0.927	High Similarity	NPC81638
0.927	High Similarity	NPC477616
0.9265	High Similarity	NPC311530
0.9265	High Similarity	NPC265075
0.9259	High Similarity	NPC184613
0.9259	High Similarity	NPC22517
0.9248	High Similarity	NPC287745
0.9242	High Similarity	NPC184447
0.9242	High Similarity	NPC175067
0.9242	High Similarity	NPC16208
0.9242	High Similarity	NPC35932
0.9242	High Similarity	NPC204215
0.9242	High Similarity	NPC7903
0.9242	High Similarity	NPC470752
0.9242	High Similarity	NPC160991
0.9237	High Similarity	NPC234488
0.9237	High Similarity	NPC299221
0.9237	High Similarity	NPC214860
0.9237	High Similarity	NPC224157
0.9237	High Similarity	NPC472338
0.9237	High Similarity	NPC192687
0.9237	High Similarity	NPC311680
0.9237	High Similarity	NPC51840
0.9237	High Similarity	NPC126836
0.9231	High Similarity	NPC31707
0.9231	High Similarity	NPC154866
0.9225	High Similarity	NPC283049
0.9225	High Similarity	NPC44748
0.9225	High Similarity	NPC50315
0.9225	High Similarity	NPC78974
0.9225	High Similarity	NPC214406
0.9225	High Similarity	NPC223136
0.9225	High Similarity	NPC28730
0.9225	High Similarity	NPC26879
0.9225	High Similarity	NPC103823
0.9225	High Similarity	NPC18924
0.9225	High Similarity	NPC76451
0.9225	High Similarity	NPC230479
0.9209	High Similarity	NPC324492
0.9209	High Similarity	NPC190714
0.9209	High Similarity	NPC233980
0.9209	High Similarity	NPC260397
0.9209	High Similarity	NPC99515
0.9209	High Similarity	NPC317053
0.9203	High Similarity	NPC317237
0.9203	High Similarity	NPC469795
0.9203	High Similarity	NPC277951
0.9203	High Similarity	NPC44530
0.9185	High Similarity	NPC477938
0.9185	High Similarity	NPC94994
0.9179	High Similarity	NPC313081
0.9179	High Similarity	NPC134968
0.9179	High Similarity	NPC99572
0.9179	High Similarity	NPC126409
0.9179	High Similarity	NPC256262
0.9173	High Similarity	NPC36661
0.9167	High Similarity	NPC309787
0.916	High Similarity	NPC285339
0.916	High Similarity	NPC86030
0.916	High Similarity	NPC10225
0.916	High Similarity	NPC190144
0.916	High Similarity	NPC222004
0.916	High Similarity	NPC202582
0.916	High Similarity	NPC212015
0.916	High Similarity	NPC273295

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 NPC270456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	907
0.2-0.3	1834
0.3-0.4	2684
0.4-0.5	1621
0.5-0.6	872
0.6-0.7	661
0.7-0.8	169
0.8-0.85	13
0.85-0.9	5
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9389	High Similarity	NPD1612	Clinical (unspecified phase)
0.9389	High Similarity	NPD1613	Approved
0.938	High Similarity	NPD1529	Clinical (unspecified phase)
0.9302	High Similarity	NPD1530	Clinical (unspecified phase)
0.916	High Similarity	NPD3027	Phase 3
0.8939	High Similarity	NPD4908	Phase 1
0.8837	High Similarity	NPD1610	Phase 2
0.8806	High Similarity	NPD4907	Clinical (unspecified phase)
0.8514	High Similarity	NPD1934	Approved
0.8444	Intermediate Similarity	NPD2861	Phase 2
0.8421	Intermediate Similarity	NPD4749	Approved
0.8385	Intermediate Similarity	NPD1548	Phase 1
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD4625	Phase 3
0.8261	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2801	Approved
0.8175	Intermediate Similarity	NPD3018	Phase 2
0.814	Intermediate Similarity	NPD5283	Phase 1
0.8121	Intermediate Similarity	NPD1653	Approved
0.8105	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6166	Phase 2
0.8089	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD2982	Phase 2
0.8015	Intermediate Similarity	NPD2983	Phase 2
0.8014	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD6234	Discontinued
0.7987	Intermediate Similarity	NPD3882	Suspended
0.7984	Intermediate Similarity	NPD228	Approved
0.7973	Intermediate Similarity	NPD1511	Approved
0.7945	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6674	Discontinued
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7898	Intermediate Similarity	NPD7199	Phase 2
0.7888	Intermediate Similarity	NPD7074	Phase 3
0.7867	Intermediate Similarity	NPD1512	Approved
0.7829	Intermediate Similarity	NPD3021	Approved
0.7829	Intermediate Similarity	NPD3022	Approved
0.7826	Intermediate Similarity	NPD7054	Approved
0.7806	Intermediate Similarity	NPD3817	Phase 2
0.7799	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD7472	Approved
0.7764	Intermediate Similarity	NPD7228	Approved
0.7764	Intermediate Similarity	NPD3818	Discontinued
0.7762	Intermediate Similarity	NPD3620	Phase 2
0.7762	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1558	Phase 1
0.7756	Intermediate Similarity	NPD4965	Approved
0.7756	Intermediate Similarity	NPD4966	Approved
0.7756	Intermediate Similarity	NPD4967	Phase 2
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6671	Approved
0.7742	Intermediate Similarity	NPD1465	Phase 2
0.774	Intermediate Similarity	NPD6099	Approved
0.774	Intermediate Similarity	NPD6100	Approved
0.7737	Intermediate Similarity	NPD1091	Approved
0.7722	Intermediate Similarity	NPD5494	Approved
0.7718	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5844	Phase 1
0.7714	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD8651	Approved
0.7687	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7447	Phase 1
0.7671	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4675	Approved
0.7662	Intermediate Similarity	NPD4678	Approved
0.7636	Intermediate Similarity	NPD7549	Discontinued
0.7626	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6797	Phase 2
0.7616	Intermediate Similarity	NPD7213	Phase 3
0.7616	Intermediate Similarity	NPD7212	Phase 2
0.7615	Intermediate Similarity	NPD2684	Approved
0.7612	Intermediate Similarity	NPD7157	Approved
0.7609	Intermediate Similarity	NPD422	Phase 1
0.7609	Intermediate Similarity	NPD3705	Approved
0.7603	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4538	Approved
0.7603	Intermediate Similarity	NPD4536	Approved
0.7586	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5124	Phase 1
0.7584	Intermediate Similarity	NPD5177	Phase 3
0.7584	Intermediate Similarity	NPD1652	Phase 2
0.7576	Intermediate Similarity	NPD7251	Discontinued
0.7568	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3540	Phase 1
0.7568	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7266	Discontinued
0.7566	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4380	Phase 2
0.7545	Intermediate Similarity	NPD8053	Approved
0.7545	Intermediate Similarity	NPD8054	Approved
0.7533	Intermediate Similarity	NPD3892	Phase 2
0.7533	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7808	Phase 3
0.753	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7843	Approved
0.7517	Intermediate Similarity	NPD1549	Phase 2
0.7516	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6232	Discontinued
0.7515	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3539	Phase 1
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7484	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4005	Discontinued
0.7484	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7075	Discontinued
0.7468	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6355	Discontinued
0.7465	Intermediate Similarity	NPD6584	Phase 3
0.7451	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7124	Phase 2
0.7432	Intermediate Similarity	NPD5588	Approved
0.7432	Intermediate Similarity	NPD5960	Phase 3
0.7431	Intermediate Similarity	NPD7095	Approved
0.7424	Intermediate Similarity	NPD4750	Phase 3
0.7417	Intermediate Similarity	NPD3750	Approved
0.7417	Intermediate Similarity	NPD6331	Phase 2
0.7417	Intermediate Similarity	NPD7466	Approved
0.7405	Intermediate Similarity	NPD290	Approved
0.7405	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7819	Suspended
0.7389	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7372	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2677	Approved
0.7358	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5735	Approved
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7338	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5846	Approved
0.7338	Intermediate Similarity	NPD6516	Phase 2
0.7333	Intermediate Similarity	NPD5763	Approved
0.7333	Intermediate Similarity	NPD5762	Approved
0.7333	Intermediate Similarity	NPD1375	Discontinued
0.7328	Intermediate Similarity	NPD968	Approved
0.732	Intermediate Similarity	NPD5058	Phase 3
0.7317	Intermediate Similarity	NPD27	Approved
0.7317	Intermediate Similarity	NPD2489	Approved
0.7315	Intermediate Similarity	NPD1510	Phase 2
0.7303	Intermediate Similarity	NPD4110	Phase 3
0.7303	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7279	Intermediate Similarity	NPD2238	Phase 2
0.7278	Intermediate Similarity	NPD4577	Approved
0.7278	Intermediate Similarity	NPD4578	Approved
0.7278	Intermediate Similarity	NPD7313	Approved
0.7278	Intermediate Similarity	NPD7310	Approved
0.7278	Intermediate Similarity	NPD7312	Approved
0.7278	Intermediate Similarity	NPD7311	Approved
0.7273	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2797	Approved
0.7267	Intermediate Similarity	NPD2796	Approved
0.7262	Intermediate Similarity	NPD7240	Approved
0.7262	Intermediate Similarity	NPD6559	Discontinued
0.7256	Intermediate Similarity	NPD2969	Approved
0.7256	Intermediate Similarity	NPD2970	Approved
0.7254	Intermediate Similarity	NPD6582	Phase 2
0.7254	Intermediate Similarity	NPD6583	Phase 3
0.7251	Intermediate Similarity	NPD4663	Approved
0.7248	Intermediate Similarity	NPD6111	Discontinued
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7241	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6959	Discontinued
0.7237	Intermediate Similarity	NPD3060	Approved
0.7235	Intermediate Similarity	NPD7309	Approved
0.723	Intermediate Similarity	NPD230	Phase 1
0.7215	Intermediate Similarity	NPD6599	Discontinued
0.7211	Intermediate Similarity	NPD6233	Phase 2
0.7209	Intermediate Similarity	NPD7906	Approved
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.7205	Intermediate Similarity	NPD7768	Phase 2
0.7203	Intermediate Similarity	NPD6696	Suspended
0.7195	Intermediate Similarity	NPD7229	Phase 3
0.7195	Intermediate Similarity	NPD3051	Approved
0.7195	Intermediate Similarity	NPD3787	Discontinued
0.7193	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4628	Phase 3
0.7186	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD8156	Discontinued
0.7183	Intermediate Similarity	NPD1608	Approved
0.7171	Intermediate Similarity	NPD2424	Discontinued
0.7171	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6072	Discontinued
0.717	Intermediate Similarity	NPD7411	Suspended
0.7163	Intermediate Similarity	NPD3496	Discontinued
0.7162	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1774	Approved
0.716	Intermediate Similarity	NPD4055	Discovery
0.7152	Intermediate Similarity	NPD2161	Phase 2
0.7143	Intermediate Similarity	NPD2563	Approved
0.7143	Intermediate Similarity	NPD5111	Phase 2

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