NPASS Compound

Structure

CID277532 OpenBabel06191716082D 54 58 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 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 4.3301 -1.5000 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 5.1962 -1.0000 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 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 1.5000 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 9.5263 0.5000 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 5.1962 0.0000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8301 2.3660 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 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 7.7942 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 2 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 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3923 0.0000 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 -5.3301 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8301 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 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 7.7942 -2.5000 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 6.0622 -1.5000 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 -3.3301 1.5000 0.0000 O 0 0 0 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 -2.5981 0.5000 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 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 48 1 0 0 0 0 3 5 1 0 0 0 0 3 13 2 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 7 16 1 0 0 0 0 8 15 1 0 0 0 0 8 17 2 0 0 0 0 9 20 1 0 0 0 0 9 34 1 0 0 0 0 10 21 1 0 0 0 0 10 34 1 0 0 0 0 11 35 1 0 0 0 0 12 49 1 0 0 0 0 13 30 1 0 0 0 0 14 50 1 0 0 0 0 15 48 1 0 0 0 0 16 22 2 0 0 0 0 16 36 1 0 0 0 0 17 22 1 0 0 0 0 17 51 1 0 0 0 0 18 11 1 6 0 0 0 18 23 1 0 0 0 0 18 52 1 0 0 0 0 19 12 1 6 0 0 0 19 24 1 0 0 0 0 19 53 1 0 0 0 0 20 37 2 0 0 0 0 20 38 1 0 0 0 0 21 39 2 0 0 0 0 21 49 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 23 40 1 1 0 0 0 24 27 1 0 0 0 0 24 41 1 6 0 0 0 25 31 1 0 0 0 0 25 42 2 0 0 0 0 26 28 1 0 0 0 0 26 43 1 6 0 0 0 27 29 1 0 0 0 0 27 44 1 6 0 0 0 28 32 1 0 0 0 0 28 45 1 1 0 0 0 29 33 1 0 0 0 0 29 46 1 1 0 0 0 30 31 2 0 0 0 0 30 51 1 0 0 0 0 31 54 1 0 0 0 0 32 50 1 6 0 0 0 32 52 1 0 0 0 0 33 53 1 0 0 0 0 33 54 1 6 0 0 0 34 1 1 1 0 0 0 34 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	768.21
Volume:	703.278
LogP:	-0.014
LogD:	-0.398
LogS:	-3.114
# Rotatable Bonds:	14
TPSA:	322.03
# H-Bond Aceptor:	20
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.082
Synthetic Accessibility Score:	5.093
Fsp3:	0.5
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:	-6.873
MDCK Permeability:	8.676393190398812e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.884
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	69.55096435546875%
Volume Distribution (VD):	0.46
Pgp-substrate:	17.722688674926758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.172
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.135
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.318
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.767
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.031
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC277532

Natural Product ID:	NPC277532
*Common Name:**	Oxytroflavoside E
IUPAC Name:	(3S)-3-hydroxy-3-methyl-5-oxo-5-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-7-methoxy-4-oxo-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-3-yl]oxyoxan-2-yl]methoxy]pentanoic acid
Synonyms:	Oxytroflavoside E
Standard InCHIKey:	YYHLAMZVDLNYIY-ZNNIGJCWSA-N
Standard InCHI:	InChI=1S/C34H40O20/c1-34(47,9-20(37)38)10-21(39)49-12-19-24(41)27(44)29(46)33(53-19)54-31-25(42)22-16(36)7-15(48-2)8-17(22)51-30(31)13-3-5-14(6-4-13)50-32-28(45)26(43)23(40)18(11-35)52-32/h3-8,18-19,23-24,26-29,32-33,35-36,40-41,43-47H,9-12H2,1-2H3,(H,37,38)/t18-,19-,23-,24+,26+,27+,28-,29-,32-,33+,34+/m1/s1
SMILES:	C[C@](CC(=O)O)(CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071421
PubChem CID:	60200222
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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
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]
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]
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]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	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]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	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]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	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]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	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]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	5.0	%	PMID[448260]

☑ 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 NPC277532 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	422
0.1-0.2	1752
0.2-0.3	4007
0.3-0.4	9066
0.4-0.5	9443
0.5-0.6	5162
0.6-0.7	5745
0.7-0.8	5544
0.8-0.85	772
0.85-0.9	430
0.9-0.95	319
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC209550
1.0	High Similarity	NPC138990
1.0	High Similarity	NPC175429
0.9811	High Similarity	NPC64425
0.9691	High Similarity	NPC474522
0.9688	High Similarity	NPC221342
0.9688	High Similarity	NPC476470
0.9688	High Similarity	NPC142142
0.9688	High Similarity	NPC477613
0.9688	High Similarity	NPC11432
0.9688	High Similarity	NPC186816
0.9688	High Similarity	NPC256188
0.9688	High Similarity	NPC12013
0.9688	High Similarity	NPC203145
0.9688	High Similarity	NPC32641
0.9688	High Similarity	NPC189564
0.9686	High Similarity	NPC121703
0.963	High Similarity	NPC470712
0.963	High Similarity	NPC164704
0.9625	High Similarity	NPC76831
0.9625	High Similarity	NPC287889
0.9625	High Similarity	NPC292929
0.9625	High Similarity	NPC135358
0.9625	High Similarity	NPC289667
0.9623	High Similarity	NPC298171
0.9623	High Similarity	NPC240306
0.9571	High Similarity	NPC470716
0.9571	High Similarity	NPC470715
0.9571	High Similarity	NPC470714
0.9565	High Similarity	NPC68592
0.9565	High Similarity	NPC262222
0.9565	High Similarity	NPC298666
0.956	High Similarity	NPC64305
0.956	High Similarity	NPC48093
0.956	High Similarity	NPC215710
0.956	High Similarity	NPC135846
0.956	High Similarity	NPC101636
0.956	High Similarity	NPC163242
0.956	High Similarity	NPC253788
0.956	High Similarity	NPC276377
0.956	High Similarity	NPC173582
0.956	High Similarity	NPC473438
0.956	High Similarity	NPC476215
0.956	High Similarity	NPC224530
0.956	High Similarity	NPC297987
0.956	High Similarity	NPC246943
0.956	High Similarity	NPC265885
0.956	High Similarity	NPC139320
0.956	High Similarity	NPC170052
0.956	High Similarity	NPC216496
0.956	High Similarity	NPC129217
0.956	High Similarity	NPC85707
0.956	High Similarity	NPC259957
0.956	High Similarity	NPC159579
0.956	High Similarity	NPC116458
0.956	High Similarity	NPC249281
0.956	High Similarity	NPC181465
0.9515	High Similarity	NPC231787
0.9503	High Similarity	NPC72016
0.95	High Similarity	NPC244875
0.95	High Similarity	NPC27942
0.95	High Similarity	NPC475382
0.9497	High Similarity	NPC136761
0.9497	High Similarity	NPC470405
0.9497	High Similarity	NPC187379
0.9497	High Similarity	NPC304741
0.9497	High Similarity	NPC471079
0.9451	High Similarity	NPC11847
0.9451	High Similarity	NPC217822
0.9451	High Similarity	NPC101399
0.9451	High Similarity	NPC221288
0.9448	High Similarity	NPC5319
0.9441	High Similarity	NPC473644
0.9441	High Similarity	NPC311850
0.9437	High Similarity	NPC282169
0.9434	High Similarity	NPC41121
0.9434	High Similarity	NPC320283
0.9434	High Similarity	NPC472459
0.9434	High Similarity	NPC111929
0.9434	High Similarity	NPC104677
0.9434	High Similarity	NPC22062
0.9434	High Similarity	NPC138811
0.9434	High Similarity	NPC473634
0.9398	High Similarity	NPC89127
0.9398	High Similarity	NPC471669
0.9398	High Similarity	NPC473862
0.939	High Similarity	NPC280642
0.939	High Similarity	NPC218161
0.939	High Similarity	NPC469344
0.939	High Similarity	NPC92815
0.939	High Similarity	NPC188815
0.939	High Similarity	NPC96605
0.9383	High Similarity	NPC205824
0.9383	High Similarity	NPC139060
0.9383	High Similarity	NPC85751
0.9383	High Similarity	NPC129264
0.9383	High Similarity	NPC19240
0.9379	High Similarity	NPC150164
0.9375	High Similarity	NPC473623
0.9375	High Similarity	NPC153342
0.9375	High Similarity	NPC321478
0.9371	High Similarity	NPC108831
0.9371	High Similarity	NPC135391
0.9371	High Similarity	NPC182634
0.9371	High Similarity	NPC65003
0.9371	High Similarity	NPC197304
0.9371	High Similarity	NPC473512
0.9371	High Similarity	NPC77672
0.9371	High Similarity	NPC78263
0.9371	High Similarity	NPC44931
0.9371	High Similarity	NPC54802
0.9371	High Similarity	NPC133671
0.9371	High Similarity	NPC129827
0.9341	High Similarity	NPC173837
0.9321	High Similarity	NPC80068
0.9317	High Similarity	NPC470125
0.9317	High Similarity	NPC473516
0.9308	High Similarity	NPC323593
0.9308	High Similarity	NPC203500
0.9308	High Similarity	NPC307938
0.9308	High Similarity	NPC473657
0.9308	High Similarity	NPC295613
0.929	High Similarity	NPC162394
0.929	High Similarity	NPC156785
0.929	High Similarity	NPC241781
0.9281	High Similarity	NPC48984
0.9281	High Similarity	NPC122467
0.9281	High Similarity	NPC14187
0.9281	High Similarity	NPC202908
0.9281	High Similarity	NPC292019
0.9255	High Similarity	NPC271270
0.9255	High Similarity	NPC142860
0.9255	High Similarity	NPC97285
0.9255	High Similarity	NPC246469
0.925	High Similarity	NPC117478
0.9245	High Similarity	NPC27408
0.9245	High Similarity	NPC95090
0.924	High Similarity	NPC282636
0.924	High Similarity	NPC294863
0.9235	High Similarity	NPC460984
0.9235	High Similarity	NPC223860
0.9235	High Similarity	NPC25946
0.9235	High Similarity	NPC470717
0.9235	High Similarity	NPC21359
0.9235	High Similarity	NPC470451
0.9235	High Similarity	NPC249560
0.9235	High Similarity	NPC106700
0.9235	High Similarity	NPC470713
0.9235	High Similarity	NPC470720
0.9235	High Similarity	NPC75574
0.9235	High Similarity	NPC275977
0.9235	High Similarity	NPC470455
0.9226	High Similarity	NPC251417
0.9226	High Similarity	NPC89052
0.9222	High Similarity	NPC19108
0.9222	High Similarity	NPC473327
0.9222	High Similarity	NPC294815
0.9222	High Similarity	NPC253685
0.9222	High Similarity	NPC476472
0.9222	High Similarity	NPC16194
0.9222	High Similarity	NPC220173
0.9217	High Similarity	NPC134532
0.9217	High Similarity	NPC33054
0.9217	High Similarity	NPC137871
0.9217	High Similarity	NPC257011
0.9217	High Similarity	NPC471748
0.9217	High Similarity	NPC471725
0.9217	High Similarity	NPC288152
0.9217	High Similarity	NPC155877
0.9217	High Similarity	NPC176740
0.9217	High Similarity	NPC9002
0.9217	High Similarity	NPC203259
0.9207	High Similarity	NPC473278
0.9207	High Similarity	NPC89809
0.9207	High Similarity	NPC260504
0.9202	High Similarity	NPC179198
0.9202	High Similarity	NPC183672
0.9202	High Similarity	NPC278419
0.9202	High Similarity	NPC257566
0.9202	High Similarity	NPC124155
0.9202	High Similarity	NPC66087
0.9198	High Similarity	NPC477629
0.9198	High Similarity	NPC210961
0.9198	High Similarity	NPC270675
0.9198	High Similarity	NPC303913
0.9198	High Similarity	NPC195685
0.9198	High Similarity	NPC472994
0.9198	High Similarity	NPC477628
0.9187	High Similarity	NPC206378
0.9187	High Similarity	NPC127406
0.9182	High Similarity	NPC143851
0.9182	High Similarity	NPC83283
0.9182	High Similarity	NPC29763
0.9182	High Similarity	NPC39360
0.9182	High Similarity	NPC210003
0.9181	High Similarity	NPC470719
0.9181	High Similarity	NPC33083
0.9181	High Similarity	NPC473554
0.9181	High Similarity	NPC295625
0.9176	High Similarity	NPC470446

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 NPC277532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	936
0.2-0.3	1967
0.3-0.4	2748
0.4-0.5	1929
0.5-0.6	832
0.6-0.7	234
0.7-0.8	107
0.8-0.85	18
0.85-0.9	3
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9448	High Similarity	NPD7804	Clinical (unspecified phase)
0.9337	High Similarity	NPD7808	Phase 3
0.9277	High Similarity	NPD7251	Discontinued
0.9217	High Similarity	NPD6797	Phase 2
0.9042	High Similarity	NPD7472	Approved
0.9012	High Similarity	NPD4381	Clinical (unspecified phase)
0.8982	High Similarity	NPD7054	Approved
0.8882	High Similarity	NPD4338	Clinical (unspecified phase)
0.8817	High Similarity	NPD7074	Phase 3
0.878	High Similarity	NPD7075	Discontinued
0.865	High Similarity	NPD6801	Discontinued
0.8598	High Similarity	NPD7096	Clinical (unspecified phase)
0.8571	High Similarity	NPD5403	Approved
0.85	High Similarity	NPD6799	Approved
0.8471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6166	Phase 2
0.8471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD5401	Approved
0.8434	Intermediate Similarity	NPD3817	Phase 2
0.8415	Intermediate Similarity	NPD4380	Phase 2
0.838	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD3818	Discontinued
0.8323	Intermediate Similarity	NPD5402	Approved
0.8253	Intermediate Similarity	NPD7411	Suspended
0.8229	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6599	Discontinued
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1934	Approved
0.809	Intermediate Similarity	NPD8312	Approved
0.809	Intermediate Similarity	NPD8313	Approved
0.8075	Intermediate Similarity	NPD1549	Phase 2
0.8047	Intermediate Similarity	NPD7819	Suspended
0.8047	Intermediate Similarity	NPD8455	Phase 2
0.8047	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3882	Suspended
0.7953	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD1512	Approved
0.7941	Intermediate Similarity	NPD2801	Approved
0.7903	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3751	Discontinued
0.7842	Intermediate Similarity	NPD7435	Discontinued
0.784	Intermediate Similarity	NPD2796	Approved
0.7831	Intermediate Similarity	NPD1511	Approved
0.7829	Intermediate Similarity	NPD3787	Discontinued
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7758	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7768	Phase 2
0.7736	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD8151	Discontinued
0.772	Intermediate Similarity	NPD7584	Approved
0.7692	Intermediate Similarity	NPD7874	Approved
0.7692	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7685	Pre-registration
0.7656	Intermediate Similarity	NPD7698	Approved
0.7656	Intermediate Similarity	NPD7697	Approved
0.7656	Intermediate Similarity	NPD7696	Phase 3
0.7653	Intermediate Similarity	NPD7783	Phase 2
0.7653	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3750	Approved
0.764	Intermediate Similarity	NPD1240	Approved
0.764	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD8320	Phase 1
0.7617	Intermediate Similarity	NPD8319	Approved
0.76	Intermediate Similarity	NPD3749	Approved
0.7592	Intermediate Similarity	NPD6779	Approved
0.7592	Intermediate Similarity	NPD6781	Approved
0.7592	Intermediate Similarity	NPD6776	Approved
0.7592	Intermediate Similarity	NPD6780	Approved
0.7592	Intermediate Similarity	NPD6777	Approved
0.7592	Intermediate Similarity	NPD6778	Approved
0.7592	Intermediate Similarity	NPD6782	Approved
0.759	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7701	Phase 2
0.7568	Intermediate Similarity	NPD8434	Phase 2
0.7556	Intermediate Similarity	NPD7228	Approved
0.7546	Intermediate Similarity	NPD1607	Approved
0.7545	Intermediate Similarity	NPD4628	Phase 3
0.7544	Intermediate Similarity	NPD1653	Approved
0.753	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7515	Intermediate Similarity	NPD1551	Phase 2
0.7514	Intermediate Similarity	NPD5494	Approved
0.7514	Intermediate Similarity	NPD5844	Phase 1
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7585	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7033	Discontinued
0.7449	Intermediate Similarity	NPD7583	Approved
0.743	Intermediate Similarity	NPD6232	Discontinued
0.7429	Intermediate Similarity	NPD1465	Phase 2
0.7407	Intermediate Similarity	NPD6798	Discontinued
0.7399	Intermediate Similarity	NPD7458	Discontinued
0.7394	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6832	Phase 2
0.7387	Intermediate Similarity	NPD7801	Approved
0.7384	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7378	Intermediate Similarity	NPD1933	Approved
0.7374	Intermediate Similarity	NPD7199	Phase 2
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7362	Intermediate Similarity	NPD6233	Phase 2
0.736	Intermediate Similarity	NPD919	Approved
0.7349	Intermediate Similarity	NPD3748	Approved
0.733	Intermediate Similarity	NPD6534	Approved
0.733	Intermediate Similarity	NPD6535	Approved
0.7322	Intermediate Similarity	NPD7286	Phase 2
0.7317	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7240	Approved
0.7294	Intermediate Similarity	NPD6190	Approved
0.7283	Intermediate Similarity	NPD920	Approved
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.7243	Intermediate Similarity	NPD5953	Discontinued
0.7205	Intermediate Similarity	NPD1203	Approved
0.7202	Intermediate Similarity	NPD2935	Discontinued
0.7195	Intermediate Similarity	NPD3268	Approved
0.7186	Intermediate Similarity	NPD7097	Phase 1
0.7182	Intermediate Similarity	NPD1247	Approved
0.7176	Intermediate Similarity	NPD1243	Approved
0.7175	Intermediate Similarity	NPD37	Approved
0.717	Intermediate Similarity	NPD1091	Approved
0.7168	Intermediate Similarity	NPD2532	Approved
0.7168	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2533	Approved
0.7168	Intermediate Similarity	NPD2534	Approved
0.7167	Intermediate Similarity	NPD6234	Discontinued
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4966	Approved
0.7151	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3225	Approved
0.7126	Intermediate Similarity	NPD6651	Approved
0.7119	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3226	Approved
0.7093	Intermediate Similarity	NPD3887	Approved
0.7093	Intermediate Similarity	NPD2354	Approved
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7076	Intermediate Similarity	NPD2800	Approved
0.7074	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD422	Phase 1
0.7062	Intermediate Similarity	NPD4363	Phase 3
0.7062	Intermediate Similarity	NPD4360	Phase 2
0.7048	Intermediate Similarity	NPD4062	Phase 3
0.7041	Intermediate Similarity	NPD2799	Discontinued
0.7035	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7930	Approved
0.7019	Intermediate Similarity	NPD9717	Approved
0.7011	Intermediate Similarity	NPD3926	Phase 2
0.7006	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD2797	Approved
0.697	Remote Similarity	NPD4908	Phase 1
0.6964	Remote Similarity	NPD230	Phase 1
0.6964	Remote Similarity	NPD4340	Discontinued
0.6957	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2798	Approved
0.6941	Remote Similarity	NPD4308	Phase 3
0.6932	Remote Similarity	NPD5049	Phase 3
0.6918	Remote Similarity	NPD1548	Phase 1
0.6905	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7799	Discontinued
0.689	Remote Similarity	NPD3267	Approved
0.689	Remote Similarity	NPD3266	Approved
0.6889	Remote Similarity	NPD6844	Discontinued
0.6886	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2403	Approved
0.6866	Remote Similarity	NPD7680	Approved
0.6864	Remote Similarity	NPD447	Suspended
0.6864	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2353	Approved
0.686	Remote Similarity	NPD2346	Discontinued
0.686	Remote Similarity	NPD2344	Approved
0.686	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6213	Phase 3
0.6837	Remote Similarity	NPD6212	Phase 3
0.6834	Remote Similarity	NPD8285	Discontinued
0.6834	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5890	Approved
0.6833	Remote Similarity	NPD5889	Approved
0.6826	Remote Similarity	NPD7095	Approved
0.6818	Remote Similarity	NPD7390	Discontinued

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