NPASS Compound

Structure

NPC131969 OpenBabel06302216122D 45 51 0 0 1 0 0 0 0 0999 V2000 1.0783 -0.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5979 0.3453 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5978 1.0358 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0003 1.3811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 2.0714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5987 2.4166 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1966 2.0711 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1964 1.3808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7943 1.0353 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4321 1.2663 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1067 1.3910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1079 0.4399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4322 0.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9329 0.3559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5938 1.5028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0931 1.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2547 2.6497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9168 2.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4175 2.3699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2559 1.6985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7942 0.3448 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.7976 0.6903 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0388 0.8927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3537 0.8927 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8262 2.1903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5949 0.6903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6496 0.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4921 0.1074 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6291 -0.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8487 -0.0355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9312 0.1704 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6147 0.2683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0413 -0.2746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6958 1.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3382 1.7266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8787 1.2969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1962 -0.0002 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5983 0.3450 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5985 1.0355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0525 1.2656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5548 2.6068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5989 3.1072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2627 3.2973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1575 1.3590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 39 1 0 0 0 0 2 3 1 0 0 0 0 2 10 1 0 0 0 0 3 4 1 0 0 0 0 3 45 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 6 43 1 0 0 0 0 7 11 1 0 0 0 0 7 8 1 0 0 0 0 7 42 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 15 20 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 21 31 1 0 0 0 0 21 37 1 0 0 0 0 21 22 1 0 0 0 0 22 39 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 28 29 1 0 0 0 0 28 34 1 0 0 0 0 28 37 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 31 32 1 0 0 0 0 32 33 1 0 0 0 0 34 35 1 0 0 0 0 35 36 1 0 0 0 0 37 38 1 0 0 0 0 38 39 1 0 0 0 0 38 40 1 0 0 0 0 40 41 1 0 0 0 0 43 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	627.38
Volume:	642.089
LogP:	2.314
LogD:	2.538
LogS:	-4.343
# Rotatable Bonds:	8
TPSA:	106.92
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	7.232
Fsp3:	0.806
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:	-5.154
MDCK Permeability:	6.180406489875168e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.292
Human Intestinal Absorption (HIA):	0.452
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.533

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.238
Plasma Protein Binding (PPB):	24.19798469543457%
Volume Distribution (VD):	4.926
Pgp-substrate:	44.506107330322266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.806
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.775

ADMET: Excretion

Clearance (CL):	12.289
Half-life (T1/2):	0.006

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.339
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.026
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC131969

Natural Product ID:	NPC131969
*Common Name:**	OSOKHVIUAUBKGK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OSOKHVIUAUBKGK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C36H53NO8/c1-33-24(38)12-13-25(42-4)35(40)18-22(28(33)31(35)45-32(39)21-10-8-7-9-11-21)36-23-19-37(2)17-16-34(20-41-3,15-14-26(36)43-5)30(36)29(44-6)27(23)33/h7-11,22-31,38,40H,12-20H2,1-6H3
SMILES:	CC12C(CCC(C3(CC(C2C3OC(=O)c2ccccc2)C23C4CN(C)CCC(CCC2OC)(COC)C3C(C14)OC)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11858758]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	tuber	n.a.	PMID[12913245]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1293938]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15374592]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16181762]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	flowers	Yuxi Town, Fuqing City, Fujian Province, China	2005-SEP	PMID[17583953]
NPO21393	Datura inoxia	Species	Solanaceae	Eukaryota	n.a.	flower	n.a.	PMID[21280589]
NPO21393	Datura inoxia	Species	Solanaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21280589]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22223386]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Lateral roots	n.a.	n.a.	PMID[22607495]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22628040]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22907155]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23225552]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23707213]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23707213]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23876370]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24170571]
NPO2245	Aconitum brachypodum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24791539]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24793215]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[27761113]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[300080]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[300080]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30892884]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO29159.1	Aconitum bullatifolium var. homotrichum	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2245	Aconitum brachypodum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20729	Aconitum coreanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29861	Aconitum carmichaeli	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19181	Przewalskia tangutica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29740	Datura innoxia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21393	Datura inoxia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2245	Aconitum brachypodum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16784	Radix aconiti lateralis preparata	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14886	Radix aconiti kusnezoffii	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19182	Radix aconiti lateralis praeparata	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19181	Przewalskia tangutica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29159.1	Aconitum bullatifolium var. homotrichum	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20729	Aconitum coreanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29740	Datura innoxia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2245	Aconitum brachypodum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29159.1	Aconitum bullatifolium var. homotrichum	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29861	Aconitum carmichaeli	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24850	Datura metel	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25993	Atropa belladonna	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19181	Przewalskia tangutica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21393	Datura inoxia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2245	Aconitum brachypodum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6495	Datura stramonium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20729	Aconitum coreanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18781	Hyoscyamus niger	Species	Solanaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC131969 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	247
0.1-0.2	1012
0.2-0.3	2310
0.3-0.4	5360
0.4-0.5	14234
0.5-0.6	16579
0.6-0.7	2424
0.7-0.8	496
0.8-0.85	35
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID

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 NPC131969 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	559
0.2-0.3	1150
0.3-0.4	2475
0.4-0.5	3157
0.5-0.6	1402
0.6-0.7	237
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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