NPASS Compound

Structure

CID242028 OpenBabel06191716042D 29 31 0 0 1 0 0 0 0 0999 V2000 -5.1962 -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 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 -3.4641 2.0000 0.0000 C 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 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 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 -0.0000 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 2 2 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 6 13 2 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 21 1 0 0 0 0 12 22 1 0 0 0 0 13 28 1 0 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 9 1 1 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 28 1 1 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.13
Volume:	389.464
LogP:	0.934
LogD:	0.814
LogS:	-1.732
# Rotatable Bonds:	5
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	3.81
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.314
MDCK Permeability:	5.390444584918441e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.64
Human Intestinal Absorption (HIA):	0.389
20% Bioavailability (F20%):	0.102
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	97.8287124633789%
Volume Distribution (VD):	0.578
Pgp-substrate:	1.8035980463027954%

ADMET: Metabolism

CYP1A2-inhibitor:	0.311
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.368
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.457
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	10.039
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.253
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.449
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.957
Carcinogencity:	0.171
Eye Corrosion:	0.003
Eye Irritation:	0.153
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC242028

Natural Product ID:	NPC242028
*Common Name:**	(E)-Astringin
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	(E)-Astringin
Standard InCHIKey:	PERPNFLGJXUDDW-CUYWLFDKSA-N
Standard InCHI:	InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
SMILES:	C(=Cc1cc(cc(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL358769
PubChem CID:	5281712
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene 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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80°N and longitude 4°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.bse.2004.02.008]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/01496395.2011.635623]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11324918]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497936]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	stem bark	Veikabu bridge along the Hiritano highway 40 km from Port Moresby, Papua New Guinea	1998-FEB	PMID[16038553]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
NPO21036	Celaenodendron mexicanum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19299148]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19863101]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121250]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20973551]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25611131]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[464561]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7513747]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561895]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30422	Picea sp	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31130	Eucalyptus sp	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11861	Rheum sp.	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22269	Eucalyptus sp.	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3401	Picea sp.	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11861	Rheum sp.	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16089	Dumortiera hirsuta	Species	Dumortieraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14395	Lysimachia mauritiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16493	Nasutitermes ephratae	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17544	Acacia adunca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19969	Dermocybe canaria	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17400	Peltostigma guatemalense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17472	Drechslera avenae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11538	Salvia syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7562	Premna odorata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21164	Veratrum dahuricum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17633	Viguiera incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4325	Blastochloris viridis	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2507	Rumex maritimus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21918	Aconitum heterophylloides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18859	Carica pennata	Species	Caricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16369	Lepisorus ussuriensis	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17865	Amathia pinnata	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10417	Ipomoea digitata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20715	Astragalus cibarius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12703	Eucalyptus melliodora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13407	Goniothalamus malayanus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17169	Adiantum lunulatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21542	Vernonia menthaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21724	Sabina sargentii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18022	Naucleopsis ternstroemiiflora	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17942	Wikstroemia retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8506	Cotyledon secunda	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10989	Annona cornifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15552	Anacystis montana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14859	Bishovia boliviensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21036	Celaenodendron mexicanum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17242	Laurencia spectabilis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17130	Hylotelephium telephium	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17786	Marrubium anisodon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16731	Phoebe pittieri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15227	Helipterum roseum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17702	Astragalus sempervirens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3964	Calostephane divaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15803	Artemisia assoana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15467	Hedysarum connatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16611	Alstonia spathulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6881	Caragana aurantiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13642	Pastinaca sativa	Species	Apiaceae	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
IC50	3
Others	3

Activity Type	# Activity
NON-MOLECULAR	1
Others	3
Protein Family	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	30600.0	nM	PMID[506390]
NPT2	Others	Unspecified		Relative IC50	=	2.42	n.a.	PMID[506390]
NPT1	Others	Radical scavenging activity		IC50	=	30200.0	nM	PMID[506391]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[506391]
NPT544	Protein Family	Estrogen receptor	Homo sapiens	FC	=	1.1	n.a.	PMID[506394]

☑ 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 NPC242028 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	429
0.1-0.2	1752
0.2-0.3	5334
0.3-0.4	11304
0.4-0.5	6446
0.5-0.6	5210
0.6-0.7	6909
0.7-0.8	4050
0.8-0.85	860
0.85-0.9	303
0.9-0.95	77
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC203230
0.9923	High Similarity	NPC59324
0.9923	High Similarity	NPC65530
0.9847	High Similarity	NPC212770
0.9847	High Similarity	NPC98777
0.9699	High Similarity	NPC469661
0.969	High Similarity	NPC303422
0.969	High Similarity	NPC85799
0.969	High Similarity	NPC165686
0.969	High Similarity	NPC26080
0.9627	High Similarity	NPC189115
0.9627	High Similarity	NPC469559
0.9627	High Similarity	NPC475084
0.9615	High Similarity	NPC115022
0.9615	High Similarity	NPC294166
0.9612	High Similarity	NPC121376
0.9556	High Similarity	NPC252169
0.9556	High Similarity	NPC473044
0.9542	High Similarity	NPC188555
0.9542	High Similarity	NPC130496
0.9485	High Similarity	NPC138227
0.9485	High Similarity	NPC469313
0.9485	High Similarity	NPC168579
0.9485	High Similarity	NPC473045
0.9485	High Similarity	NPC76176
0.9485	High Similarity	NPC25292
0.947	High Similarity	NPC238243
0.9466	High Similarity	NPC49074
0.9466	High Similarity	NPC132895
0.9457	High Similarity	NPC218003
0.9416	High Similarity	NPC475096
0.9412	High Similarity	NPC37793
0.9398	High Similarity	NPC40664
0.9398	High Similarity	NPC164857
0.9398	High Similarity	NPC197723
0.9398	High Similarity	NPC3293
0.9398	High Similarity	NPC165482
0.9398	High Similarity	NPC138350
0.9389	High Similarity	NPC162093
0.9348	High Similarity	NPC190714
0.9348	High Similarity	NPC125755
0.9348	High Similarity	NPC99515
0.9328	High Similarity	NPC470413
0.9328	High Similarity	NPC138738
0.9328	High Similarity	NPC124149
0.9323	High Similarity	NPC470236
0.9281	High Similarity	NPC15538
0.9281	High Similarity	NPC39657
0.9281	High Similarity	NPC473480
0.9281	High Similarity	NPC227902
0.9275	High Similarity	NPC161700
0.9275	High Similarity	NPC277867
0.9248	High Similarity	NPC251981
0.9248	High Similarity	NPC107478
0.9248	High Similarity	NPC170694
0.9248	High Similarity	NPC13745
0.9248	High Similarity	NPC48863
0.9242	High Similarity	NPC470270
0.9242	High Similarity	NPC299144
0.9214	High Similarity	NPC478237
0.9214	High Similarity	NPC280945
0.9214	High Similarity	NPC175976
0.9197	High Similarity	NPC5262
0.9197	High Similarity	NPC472714
0.9191	High Similarity	NPC106944
0.9185	High Similarity	NPC195196
0.9173	High Similarity	NPC215833
0.9173	High Similarity	NPC69513
0.9167	High Similarity	NPC469698
0.9167	High Similarity	NPC473412
0.916	High Similarity	NPC248355
0.916	High Similarity	NPC307110
0.9149	High Similarity	NPC286235
0.9149	High Similarity	NPC55158
0.9149	High Similarity	NPC51328
0.9149	High Similarity	NPC106138
0.9124	High Similarity	NPC210192
0.9124	High Similarity	NPC257095
0.9124	High Similarity	NPC89686
0.9124	High Similarity	NPC273932
0.9124	High Similarity	NPC186406
0.9111	High Similarity	NPC25695
0.9111	High Similarity	NPC177035
0.9111	High Similarity	NPC199459
0.9111	High Similarity	NPC52277
0.9111	High Similarity	NPC172818
0.9104	High Similarity	NPC187194
0.9104	High Similarity	NPC476411
0.9104	High Similarity	NPC87696
0.9098	High Similarity	NPC160991
0.9098	High Similarity	NPC184447
0.9098	High Similarity	NPC16208
0.9098	High Similarity	NPC7903
0.9098	High Similarity	NPC35932
0.9084	High Similarity	NPC302378
0.9078	High Similarity	NPC248132
0.9078	High Similarity	NPC130449
0.9065	High Similarity	NPC118385
0.9065	High Similarity	NPC472713
0.9065	High Similarity	NPC473046
0.9065	High Similarity	NPC292443
0.9065	High Similarity	NPC187774
0.9065	High Similarity	NPC472712
0.9058	High Similarity	NPC157816
0.9037	High Similarity	NPC164787
0.9023	High Similarity	NPC166168
0.9023	High Similarity	NPC65942
0.9023	High Similarity	NPC9912
0.9023	High Similarity	NPC472597
0.9023	High Similarity	NPC475067
0.9023	High Similarity	NPC248307
0.9021	High Similarity	NPC473621
0.9015	High Similarity	NPC166040
0.9	High Similarity	NPC12308
0.8993	High Similarity	NPC478239
0.8993	High Similarity	NPC470950
0.8993	High Similarity	NPC185307
0.8993	High Similarity	NPC46092
0.8993	High Similarity	NPC81638
0.8978	High Similarity	NPC292487
0.8971	High Similarity	NPC104167
0.8971	High Similarity	NPC306441
0.8971	High Similarity	NPC16435
0.8971	High Similarity	NPC302701
0.8971	High Similarity	NPC269091
0.8963	High Similarity	NPC310854
0.8963	High Similarity	NPC35731
0.8958	High Similarity	NPC169404
0.8958	High Similarity	NPC176186
0.8958	High Similarity	NPC53587
0.8958	High Similarity	NPC21902
0.8955	High Similarity	NPC61477
0.8955	High Similarity	NPC261619
0.8955	High Similarity	NPC219876
0.8955	High Similarity	NPC201587
0.8955	High Similarity	NPC253105
0.8955	High Similarity	NPC252833
0.8955	High Similarity	NPC185604
0.8955	High Similarity	NPC78770
0.8955	High Similarity	NPC15658
0.8955	High Similarity	NPC470752
0.8955	High Similarity	NPC126029
0.8951	High Similarity	NPC472710
0.8951	High Similarity	NPC472709
0.8947	High Similarity	NPC472338
0.8947	High Similarity	NPC80600
0.8947	High Similarity	NPC472024
0.8939	High Similarity	NPC72529
0.8936	High Similarity	NPC199928
0.8929	High Similarity	NPC232228
0.8929	High Similarity	NPC129417
0.8929	High Similarity	NPC283995
0.8929	High Similarity	NPC470235
0.8929	High Similarity	NPC476867
0.8921	High Similarity	NPC476356
0.8913	High Similarity	NPC202700
0.8913	High Similarity	NPC210478
0.8905	High Similarity	NPC87777
0.8905	High Similarity	NPC262328
0.8905	High Similarity	NPC134260
0.8897	High Similarity	NPC151224
0.8897	High Similarity	NPC470356
0.8897	High Similarity	NPC234333
0.8897	High Similarity	NPC94750
0.8897	High Similarity	NPC474206
0.8897	High Similarity	NPC61946
0.8897	High Similarity	NPC260898
0.8897	High Similarity	NPC47398
0.8897	High Similarity	NPC78809
0.8897	High Similarity	NPC112246
0.8897	High Similarity	NPC112939
0.8897	High Similarity	NPC121812
0.8897	High Similarity	NPC150442
0.8889	High Similarity	NPC25821
0.8889	High Similarity	NPC6836
0.8889	High Similarity	NPC11060
0.8881	High Similarity	NPC220825
0.8881	High Similarity	NPC470095
0.8881	High Similarity	NPC309787
0.8881	High Similarity	NPC470096
0.8881	High Similarity	NPC30043
0.8881	High Similarity	NPC283839
0.8881	High Similarity	NPC90896
0.8881	High Similarity	NPC469625
0.8881	High Similarity	NPC268266
0.8881	High Similarity	NPC268342
0.8881	High Similarity	NPC469613
0.8881	High Similarity	NPC42760
0.8873	High Similarity	NPC41844
0.8872	High Similarity	NPC226788
0.8872	High Similarity	NPC210623
0.8872	High Similarity	NPC5851
0.8872	High Similarity	NPC285339
0.8872	High Similarity	NPC273295
0.8872	High Similarity	NPC218856
0.8872	High Similarity	NPC3439
0.8872	High Similarity	NPC202582
0.8872	High Similarity	NPC470633
0.8872	High Similarity	NPC222004
0.8872	High Similarity	NPC228769

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 NPC242028 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	851
0.2-0.3	2079
0.3-0.4	2807
0.4-0.5	1570
0.5-0.6	914
0.6-0.7	489
0.7-0.8	82
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8955	High Similarity	NPD1613	Approved
0.8955	High Similarity	NPD1612	Clinical (unspecified phase)
0.875	High Similarity	NPD1653	Approved
0.8731	High Similarity	NPD3027	Phase 3
0.8657	High Similarity	NPD1529	Clinical (unspecified phase)
0.8582	High Similarity	NPD1530	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD1091	Approved
0.831	Intermediate Similarity	NPD7266	Discontinued
0.8165	Intermediate Similarity	NPD7054	Approved
0.8113	Intermediate Similarity	NPD7074	Phase 3
0.8113	Intermediate Similarity	NPD7472	Approved
0.8101	Intermediate Similarity	NPD3818	Discontinued
0.8063	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.7963	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6234	Discontinued
0.7883	Intermediate Similarity	NPD2982	Phase 2
0.7883	Intermediate Similarity	NPD2983	Phase 2
0.7875	Intermediate Similarity	NPD7228	Approved
0.7871	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1610	Phase 2
0.7857	Intermediate Similarity	NPD4908	Phase 1
0.7853	Intermediate Similarity	NPD7808	Phase 3
0.7836	Intermediate Similarity	NPD1548	Phase 1
0.7823	Intermediate Similarity	NPD6674	Discontinued
0.781	Intermediate Similarity	NPD2981	Phase 2
0.7792	Intermediate Similarity	NPD1934	Approved
0.7792	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD1357	Approved
0.7756	Intermediate Similarity	NPD4967	Phase 2
0.7756	Intermediate Similarity	NPD4965	Approved
0.7756	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.766	Intermediate Similarity	NPD2861	Phase 2
0.766	Intermediate Similarity	NPD3018	Phase 2
0.764	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6166	Phase 2
0.764	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3705	Approved
0.7576	Intermediate Similarity	NPD6559	Discontinued
0.755	Intermediate Similarity	NPD5058	Phase 3
0.7516	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD6190	Approved
0.7469	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD228	Approved
0.7431	Intermediate Similarity	NPD4625	Phase 3
0.741	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8455	Phase 2
0.7403	Intermediate Similarity	NPD1512	Approved
0.7379	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4749	Approved
0.7365	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4538	Approved
0.7365	Intermediate Similarity	NPD4536	Approved
0.7365	Intermediate Similarity	NPD7240	Approved
0.7365	Intermediate Similarity	NPD7685	Pre-registration
0.7358	Intermediate Similarity	NPD3817	Phase 2
0.7351	Intermediate Similarity	NPD1652	Phase 2
0.7351	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4678	Approved
0.7325	Intermediate Similarity	NPD4380	Phase 2
0.7325	Intermediate Similarity	NPD4675	Approved
0.7315	Intermediate Similarity	NPD5588	Approved
0.7315	Intermediate Similarity	NPD5960	Phase 3
0.7312	Intermediate Similarity	NPD3882	Suspended
0.7301	Intermediate Similarity	NPD3787	Discontinued
0.7296	Intermediate Similarity	NPD2977	Approved
0.7296	Intermediate Similarity	NPD2978	Approved
0.7279	Intermediate Similarity	NPD1558	Phase 1
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7843	Approved
0.7244	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7157	Approved
0.7218	Intermediate Similarity	NPD2684	Approved
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.7206	Intermediate Similarity	NPD5283	Phase 1
0.7197	Intermediate Similarity	NPD968	Approved
0.7188	Intermediate Similarity	NPD1465	Phase 2
0.7186	Intermediate Similarity	NPD5844	Phase 1
0.7162	Intermediate Similarity	NPD3620	Phase 2
0.7162	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7114	Intermediate Similarity	NPD230	Phase 1
0.7114	Intermediate Similarity	NPD5124	Phase 1
0.7114	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD422	Phase 1
0.7105	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3540	Phase 1
0.7095	Intermediate Similarity	NPD6233	Phase 2
0.7092	Intermediate Similarity	NPD5846	Approved
0.7092	Intermediate Similarity	NPD6516	Phase 2
0.7059	Intermediate Similarity	NPD1549	Phase 2
0.7051	Intermediate Similarity	NPD7212	Phase 2
0.7051	Intermediate Similarity	NPD4357	Discontinued
0.7051	Intermediate Similarity	NPD7213	Phase 3
0.7044	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3454	Phase 3
0.7039	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3539	Phase 1
0.7037	Intermediate Similarity	NPD3022	Approved
0.7037	Intermediate Similarity	NPD3021	Approved
0.7032	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5403	Approved
0.7023	Intermediate Similarity	NPD291	Approved
0.702	Intermediate Similarity	NPD7097	Phase 1
0.7013	Intermediate Similarity	NPD3060	Approved
0.7011	Intermediate Similarity	NPD6843	Phase 3
0.7011	Intermediate Similarity	NPD6841	Approved
0.7011	Intermediate Similarity	NPD6842	Approved
0.7006	Intermediate Similarity	NPD7447	Phase 1
0.7006	Intermediate Similarity	NPD4123	Phase 3
0.7	Intermediate Similarity	NPD4340	Discontinued
0.7	Intermediate Similarity	NPD5536	Phase 2
0.6994	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1375	Discontinued
0.6986	Remote Similarity	NPD6584	Phase 3
0.6978	Remote Similarity	NPD7680	Approved
0.6978	Remote Similarity	NPD6671	Approved
0.6975	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4108	Discontinued
0.6972	Remote Similarity	NPD5126	Approved
0.6972	Remote Similarity	NPD5125	Phase 3
0.6968	Remote Similarity	NPD4628	Phase 3
0.6966	Remote Similarity	NPD8651	Approved
0.6959	Remote Similarity	NPD7095	Approved
0.6944	Remote Similarity	NPD2235	Phase 2
0.6944	Remote Similarity	NPD2231	Phase 2
0.6937	Remote Similarity	NPD4005	Discontinued
0.6936	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2677	Approved
0.6914	Remote Similarity	NPD3382	Approved
0.6914	Remote Similarity	NPD3383	Approved
0.6914	Remote Similarity	NPD6801	Discontinued
0.6914	Remote Similarity	NPD3384	Approved
0.6913	Remote Similarity	NPD6798	Discontinued
0.6912	Remote Similarity	NPD556	Approved
0.6908	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5177	Phase 3
0.6903	Remote Similarity	NPD4236	Phase 3
0.6903	Remote Similarity	NPD4162	Approved
0.6903	Remote Similarity	NPD4237	Approved
0.6899	Remote Similarity	NPD5401	Approved
0.6899	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5735	Approved
0.6886	Remote Similarity	NPD6232	Discontinued
0.6879	Remote Similarity	NPD8313	Approved
0.6879	Remote Similarity	NPD8312	Approved
0.6875	Remote Similarity	NPD3686	Approved
0.6875	Remote Similarity	NPD3687	Approved
0.6871	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7819	Suspended
0.6867	Remote Similarity	NPD5494	Approved
0.6859	Remote Similarity	NPD4535	Phase 3
0.6859	Remote Similarity	NPD3750	Approved
0.6859	Remote Similarity	NPD3892	Phase 2
0.6855	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6653	Approved
0.6835	Remote Similarity	NPD6799	Approved
0.6829	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7549	Discontinued
0.6818	Remote Similarity	NPD1551	Phase 2
0.6818	Remote Similarity	NPD6099	Approved
0.6818	Remote Similarity	NPD6100	Approved
0.6815	Remote Similarity	NPD2219	Phase 1
0.6813	Remote Similarity	NPD2122	Discontinued
0.6781	Remote Similarity	NPD6582	Phase 2
0.6781	Remote Similarity	NPD3685	Discontinued
0.6781	Remote Similarity	NPD6583	Phase 3
0.6779	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6355	Discontinued
0.6776	Remote Similarity	NPD1933	Approved
0.6774	Remote Similarity	NPD5762	Approved
0.6774	Remote Similarity	NPD5763	Approved
0.6772	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5773	Approved
0.6768	Remote Similarity	NPD5772	Approved
0.6766	Remote Similarity	NPD5677	Discontinued
0.6765	Remote Similarity	NPD7473	Discontinued
0.6763	Remote Similarity	NPD5535	Approved
0.6755	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4062	Phase 3
0.6753	Remote Similarity	NPD1510	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data