NPASS Compound

Structure

NPC62577 OpenBabel06302215222D 38 41 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 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 0.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 0.0000 2.0000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 2 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 -2.5981 0.5000 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 -3.4641 2.0000 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 -5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5902 2.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3690 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8690 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3690 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3690 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8690 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3690 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8690 -0.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8690 -2.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 O 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 -3.4641 0.0000 0.0000 C 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 0.0000 -0.0000 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 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 6 5 1 1 0 0 0 6 7 1 0 0 0 0 6 32 1 0 0 0 0 7 8 1 0 0 0 0 7 35 1 6 0 0 0 8 9 1 0 0 0 0 8 34 1 1 0 0 0 9 10 1 0 0 0 0 9 33 1 6 0 0 0 10 11 1 1 0 0 0 10 32 1 0 0 0 0 11 12 1 0 0 0 0 12 30 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 29 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 18 19 2 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 20 25 2 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 28 29 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 35 36 1 0 0 0 0 36 37 2 0 0 0 0 36 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.12
Volume:	494.639
LogP:	1.186
LogD:	0.279
LogS:	-3.909
# Rotatable Bonds:	8
TPSA:	198.51
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	4.182
Fsp3:	0.32
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.082
MDCK Permeability:	4.4831442210124806e-05
Pgp-inhibitor:	0.616
Pgp-substrate:	0.651
Human Intestinal Absorption (HIA):	0.868
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	93.84732818603516%
Volume Distribution (VD):	0.388
Pgp-substrate:	11.754794120788574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.412
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	1.49
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.674
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.85
Rat Oral Acute Toxicity:	0.744
Maximum Recommended Daily Dose:	0.763
Skin Sensitization:	0.729
Carcinogencity:	0.218
Eye Corrosion:	0.003
Eye Irritation:	0.056
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC62577

Natural Product ID:	NPC62577
*Common Name:**	ADZWGGDYJZWMBY-RCSOTXLPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ADZWGGDYJZWMBY-RCSOTXLPSA-N
Standard InCHI:	InChI=1S/C25H24O13/c1-10(26)34-9-18-24(35-11(2)27)21(32)22(33)25(38-18)37-16-6-4-13-19(30)17(36-23(13)20(16)31)8-12-3-5-14(28)15(29)7-12/h3-8,18,21-22,24-25,28-29,31-33H,9H2,1-2H3/b17-8-/t18-,21-,22-,24-,25-/m1/s1
SMILES:	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2ccc3C(=O)/C(=C/c4ccc(c(c4)O)O)/Oc3c2O)O1)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101669623
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0001738] Aurone 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
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)88710-5]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50070a031]
NPO24753	Ballota limbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15056960]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165144]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844878]
NPO25104	Grindelia scorzonerifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844947]
NPO20454	Bidens pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16041399]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209522]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17279797]
NPO28581	Aspergillus fumisynnematus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17523650]
NPO9392	Elaeodendron alluaudianum	Species	Celastraceae	Eukaryota	n.a.	Madagascar Rainforest	n.a.	PMID[19058971]
NPO9392	Elaeodendron alluaudianum	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[19058971]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19739599]
NPO23924	Psilotum nudum	Species	Psilotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20488581]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20583752]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23186307]
NPO24718	Streptomyces parvulus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23423168]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23876370]
NPO20454	Bidens pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[469551]
NPO23108	Pinus flexilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834165]
NPO24190	Uncaria sterrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23286	Galium mollugo	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23538	Ephedra distachya	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22685	Astragalus bisulcatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23924	Psilotum nudum	Species	Psilotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24190	Uncaria sterrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24753	Ballota limbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22685	Astragalus bisulcatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23286	Galium mollugo	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23853	Senegalia mellifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25266	Baccharoides lasiopus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23924	Psilotum nudum	Species	Psilotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23538	Ephedra distachya	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23538	Ephedra distachya	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22685	Astragalus bisulcatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24321	Vicia amoena	Species	Fabaceae	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]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24522	Sepia officinalis	Species	Sepiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25190	Lonchocarpus atropurpureus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23924	Psilotum nudum	Species	Psilotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22685	Astragalus bisulcatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24190	Uncaria sterrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23749	Achillea nana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO249	Dysosma pleianthum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23853	Senegalia mellifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23144	Brachyglottis bidwillii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21796	Lepidium graminifolium	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24753	Ballota limbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7066	Gomesa radicans	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25150	Haliclona cribricutis	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24321	Vicia amoena	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25266	Baccharoides lasiopus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24899	Chroogomphus helveticus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25104	Grindelia scorzonerifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23108	Pinus flexilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25129	Tricholoma acerbum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24968	Delphinus globiceps	Species	Delphinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28581	Aspergillus fumisynnematus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24112	Pisaster giganteus	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15117	Chromolaena odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25065	Gardenia imperialis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19819	Trichoderma viride	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9392	Elaeodendron alluaudianum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24020	Raputia praetermissa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23440	Aconitum napellus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22025	Drosera indica	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25225	Radianthus kuekenthali	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23365	Drummondita hassellii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24405	Farlowia mollis	Species	Dumontiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23538	Ephedra distachya	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24935	Coronilla cretica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24687	Sabadilla officinalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13694	Rhodococcus erythropolis	Species	0cardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19691	Mycena fagetorum	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23286	Galium mollugo	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24718	Streptomyces parvulus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24491	Flindersia xanthoxyla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24657	Bothriocline ripensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20454	Bidens pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17874	Mus striatus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24558	Calea lantanoides	Species	Asteraceae	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 NPC62577 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	389
0.1-0.2	1652
0.2-0.3	4007
0.3-0.4	8710
0.4-0.5	9171
0.5-0.6	4347
0.6-0.7	5101
0.7-0.8	5905
0.8-0.85	2161
0.85-0.9	931
0.9-0.95	312
0.95-1	11

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 NPC62577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	898
0.2-0.3	1972
0.3-0.4	2587
0.4-0.5	1888
0.5-0.6	935
0.6-0.7	361
0.7-0.8	126
0.8-0.85	27
0.85-0.9	13
0.9-0.95	4
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