NPASS Compound

Structure

NPC13304 OpenBabel06302216112D 24 25 0 0 1 0 0 0 0 0999 V2000 0.8660 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 2 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 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 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 1 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 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 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 -2.5000 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 4.8301 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 5 20 1 1 0 0 0 6 7 1 0 0 0 0 7 8 1 1 0 0 0 9 8 1 1 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 6 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 13 1 0 0 0 0 12 17 1 6 0 0 0 13 14 1 1 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 20 21 1 1 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.19
Volume:	338.501
LogP:	-0.679
LogD:	0.112
LogS:	-0.924
# Rotatable Bonds:	5
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	4.463
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.558
MDCK Permeability:	0.00012054775288561359
Pgp-inhibitor:	0.004
Pgp-substrate:	0.335
Human Intestinal Absorption (HIA):	0.821
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	47.075401306152344%
Volume Distribution (VD):	0.404
Pgp-substrate:	30.37359046936035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.084
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.592
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	1.624
Half-life (T1/2):	0.742

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.112
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.277
Carcinogencity:	0.07
Eye Corrosion:	0.005
Eye Irritation:	0.493
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC13304

Natural Product ID:	NPC13304
*Common Name:**	SNALOKSNSOHGKY-VQROGPIWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SNALOKSNSOHGKY-VQROGPIWSA-N
Standard InCHI:	InChI=1S/C16H30O8/c1-8-3-4-9(16(2,22)7-18)5-10(8)23-15-14(21)13(20)12(19)11(6-17)24-15/h8-15,17-22H,3-7H2,1-2H3/t8-,9-,10-,11-,12-,13+,14-,15-,16-/m1/s1
SMILES:	C[C@@H]1CC[C@H](C[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@@](C)(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94679-X]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1021/jo00272a013]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10650088]
NPO20889	Anastrepha suspensa	Species	Tephritidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10706642]
NPO20635	Dalbergia frutescens	Species	Fabaceae	Eukaryota	bark	n.a.	n.a.	PMID[11076565]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421727]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11830167]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	leaves	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	underground organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	roots and stolons	n.a.	n.a.	PMID[14738379]
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16580200]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21119678]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21473608]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21473608]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[25154406]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466012]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28245113]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30199256]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31815461]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3839140]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7684040]
NPO24658	Dillenia papuana	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798959]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19953	Lupinus formosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4785	Persicaria thunbergii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20134	Dicliptera riparia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19953	Lupinus formosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19953	Lupinus formosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22880	Aspergillus caespitosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20696	Colchicum macedonicum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22227	Sambucus ebulus	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19799	Erwinia rhapontici	Species	Erwiniaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17581	Streptomyces fulvoviridis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20134	Dicliptera riparia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20012	Wunderlichia mirabilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4785	Persicaria thunbergii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19880	Palicourea alpina	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6873	Salvia xalapensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21775	Zilla spinosa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21212	Scrophularia smithii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20190	Oxandra xylopioides	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22746	Salix sieboldiana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10757	Cyanospira rippkae	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8570	Ficus elastica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20889	Anastrepha suspensa	Species	Tephritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20953	Coprosma acerosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21839	Cymathere triplicata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22490	Limeum pterocarpum	Species	Limeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21905	Helianthopsis bishopii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20316	Hypselodoris cantabrica	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21400	Macrocystidia cucumis	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22551	Trifolium alexandrium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21270	Nerita albicilla	Species	Neritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4771	Tanacetum santolinoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22298	Inula thapsoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24658	Dillenia papuana	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22362	Tylophora flava	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20764	Euphorbia caducifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20827	Boronia muelleri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20077	Posoqueria latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15871	Parmelia enteromorpha	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22042	Kaunia arbuscularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20635	Dalbergia frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22689	Cassia carnaval	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29262	Cranfillia vulcanica	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22104	Trifolium pratense	Species	Fabaceae	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 NPC13304 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	498
0.1-0.2	4150
0.2-0.3	11769
0.3-0.4	12670
0.4-0.5	6923
0.5-0.6	4881
0.6-0.7	1592
0.7-0.8	190
0.8-0.85	9
0.85-0.9	12
0.9-0.95	2
0.95-1	1

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 NPC13304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	523
0.1-0.2	4215
0.2-0.3	2968
0.3-0.4	840
0.4-0.5	389
0.5-0.6	156
0.6-0.7	45
0.7-0.8	14
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