NPASS Compound

Structure

CID125579 OpenBabel06191715482D 34 38 0 0 1 0 0 0 0 0999 V2000 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 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 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 3.9360 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 8 2 0 0 0 0 3 16 1 0 0 0 0 4 6 1 0 0 0 0 4 18 2 0 0 0 0 5 7 2 0 0 0 0 5 18 1 0 0 0 0 6 20 2 0 0 0 0 7 20 1 0 0 0 0 8 26 1 0 0 0 0 9 17 2 0 0 0 0 9 21 1 0 0 0 0 10 17 1 0 0 0 0 10 22 2 0 0 0 0 11 16 2 0 0 0 0 11 25 1 0 0 0 0 12 19 2 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 24 2 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 25 26 2 0 0 0 0 25 27 1 0 0 0 0 26 34 1 0 0 0 0 27 19 1 1 0 0 0 27 28 1 0 0 0 0 28 18 1 6 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.14
Volume:	468.529
LogP:	4.335
LogD:	3.565
LogS:	-3.971
# Rotatable Bonds:	4
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	3.522
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.343
MDCK Permeability:	8.73009685165016e-06
Pgp-inhibitor:	0.659
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.8
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	97.1711196899414%
Volume Distribution (VD):	0.753
Pgp-substrate:	1.6690572500228882%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.688
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.327
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.989
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	14.195
Half-life (T1/2):	0.711

ADMET: Toxicity

hERG Blockers:	0.424
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.497
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.416
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.955
Carcinogencity:	0.079
Eye Corrosion:	0.004
Eye Irritation:	0.913
Respiratory Toxicity:	0.132

Download Data

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

Natural Product: NPC125579

Natural Product ID:	NPC125579
*Common Name:**	Resveratrol (E)-Dehydrodimer
IUPAC Name:	5-[(E)-2-[(2S,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]benzene-1,3-diol
Synonyms:	Resveratrol (E)-Dehydrodimer; Resveratrol Trans-Dehydrodimer
Standard InCHIKey:	LILPTCHQLRKZNG-LPGNHZEISA-N
Standard InCHI:	InChI=1S/C28H22O6/c29-20-6-4-18(5-7-20)28-27(19-12-23(32)15-24(33)13-19)25-11-16(3-8-26(25)34-28)1-2-17-9-21(30)14-22(31)10-17/h1-15,27-33H/b2-1+/t27-,28+/m0/s1
SMILES:	C(=Cc1cc(cc(c1)O)O)/c1ccc2c(c1)[C@H](c1cc(cc(c1)O)O)[C@@H](c1ccc(cc1)O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518935
PubChem CID:	10095474
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	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]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
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]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
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]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Leaf	n.a.	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]
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]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13642	Pastinaca sativa	Species	Apiaceae	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]
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]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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]
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[TCM_Taiwan]
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]
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]
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]
NPO16493	Nasutitermes ephratae	Species	Termitoidae	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]
NPO17400	Peltostigma guatemalense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4325	Blastochloris viridis	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17865	Amathia pinnata	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17633	Viguiera incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8506	Cotyledon secunda	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2507	Rumex maritimus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13407	Goniothalamus malayanus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16369	Lepisorus ussuriensis	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10989	Annona cornifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10417	Ipomoea digitata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17169	Adiantum lunulatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12703	Eucalyptus melliodora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18022	Naucleopsis ternstroemiiflora	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17942	Wikstroemia retusa	Species	Thymelaeaceae	Eukaryota	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]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	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]
NPO17242	Laurencia spectabilis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17786	Marrubium anisodon	Species	Lamiaceae	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]
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]
NPO9516	Gnetum latifolium	Species	Gnetaceae	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]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	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]
NPO3964	Calostephane divaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14395	Lysimachia mauritiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16611	Alstonia spathulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17544	Acacia adunca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17472	Drechslera avenae	Species	Pleosporaceae	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	11
MIC	1
Others	4

Activity Type	# Activity
Cell Line	5
Individual Protein	7
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	49000.0	nM	PMID[571442]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	26000.0	nM	PMID[571442]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	4300.0	nM	PMID[571443]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	3700.0	nM	PMID[571443]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	8930.0	nM	PMID[571444]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	2390.0	nM	PMID[571444]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	4300.0	nM	PMID[571445]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	>	50.0	%	PMID[571445]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	60.2	%	PMID[571445]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	80200.0	nM	PMID[571445]
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	=	48000.0	nM	PMID[571446]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	48000.0	nM	PMID[571446]
NPT2	Others	Unspecified		Ratio IC50	=	3.74	n.a.	PMID[571444]
NPT35	Others	n.a.		IC50	=	76830.0	nM	PMID[571444]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	35000.0	nM	PMID[571446]
NPT2	Others	Unspecified		Ratio	=	1.4	n.a.	PMID[571446]

☑ 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 NPC125579 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	474
0.1-0.2	1705
0.2-0.3	4190
0.3-0.4	12621
0.4-0.5	5767
0.5-0.6	4333
0.6-0.7	7712
0.7-0.8	4830
0.8-0.85	674
0.85-0.9	264
0.9-0.95	118
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC11727
0.9692	High Similarity	NPC15109
0.9618	High Similarity	NPC141717
0.9403	High Similarity	NPC174787
0.9403	High Similarity	NPC213607
0.9403	High Similarity	NPC182509
0.9323	High Similarity	NPC471522
0.9275	High Similarity	NPC14468
0.9254	High Similarity	NPC470307
0.9254	High Similarity	NPC470308
0.9237	High Similarity	NPC280653
0.9237	High Similarity	NPC300875
0.9237	High Similarity	NPC236014
0.9237	High Similarity	NPC12875
0.9237	High Similarity	NPC17343
0.9237	High Similarity	NPC164574
0.9237	High Similarity	NPC150011
0.9237	High Similarity	NPC129784
0.9237	High Similarity	NPC476166
0.9237	High Similarity	NPC129106
0.9237	High Similarity	NPC268917
0.9237	High Similarity	NPC196765
0.9237	High Similarity	NPC207892
0.9237	High Similarity	NPC118114
0.9237	High Similarity	NPC206224
0.9237	High Similarity	NPC228369
0.9209	High Similarity	NPC133209
0.9209	High Similarity	NPC6702
0.9209	High Similarity	NPC112819
0.9209	High Similarity	NPC111134
0.9197	High Similarity	NPC173203
0.9197	High Similarity	NPC163508
0.9173	High Similarity	NPC473107
0.9173	High Similarity	NPC225696
0.9173	High Similarity	NPC223008
0.9173	High Similarity	NPC476617
0.9173	High Similarity	NPC198154
0.9173	High Similarity	NPC97834
0.9173	High Similarity	NPC115335
0.9173	High Similarity	NPC476615
0.9173	High Similarity	NPC476616
0.9173	High Similarity	NPC296915
0.9167	High Similarity	NPC13005
0.916	High Similarity	NPC27187
0.916	High Similarity	NPC470225
0.916	High Similarity	NPC254000
0.9143	High Similarity	NPC20757
0.9143	High Similarity	NPC227516
0.913	High Similarity	NPC304894
0.913	High Similarity	NPC15659
0.9091	High Similarity	NPC181497
0.9091	High Similarity	NPC271945
0.9084	High Similarity	NPC471518
0.9084	High Similarity	NPC471519
0.9078	High Similarity	NPC148516
0.9078	High Similarity	NPC122980
0.9078	High Similarity	NPC177172
0.9078	High Similarity	NPC107862
0.9078	High Similarity	NPC180605
0.9065	High Similarity	NPC149633
0.9051	High Similarity	NPC277331
0.9051	High Similarity	NPC100482
0.9014	High Similarity	NPC218801
0.9008	High Similarity	NPC47283
0.9008	High Similarity	NPC39064
0.9008	High Similarity	NPC53986
0.9008	High Similarity	NPC38664
0.9	High Similarity	NPC471215
0.9	High Similarity	NPC176804
0.9	High Similarity	NPC71686
0.9	High Similarity	NPC262573
0.8955	High Similarity	NPC85435
0.8951	High Similarity	NPC105073
0.8951	High Similarity	NPC224528
0.8951	High Similarity	NPC233886
0.8951	High Similarity	NPC157081
0.8947	High Similarity	NPC211413
0.8947	High Similarity	NPC473309
0.8947	High Similarity	NPC282508
0.8947	High Similarity	NPC68205
0.8947	High Similarity	NPC293203
0.8947	High Similarity	NPC118683
0.8947	High Similarity	NPC244888
0.8947	High Similarity	NPC471517
0.8947	High Similarity	NPC164804
0.8939	High Similarity	NPC93962
0.8936	High Similarity	NPC170103
0.8936	High Similarity	NPC204770
0.8936	High Similarity	NPC224921
0.8936	High Similarity	NPC236202
0.8936	High Similarity	NPC263940
0.8936	High Similarity	NPC58190
0.8936	High Similarity	NPC202742
0.8936	High Similarity	NPC231712
0.8936	High Similarity	NPC108811
0.8936	High Similarity	NPC82917
0.8936	High Similarity	NPC237546
0.8936	High Similarity	NPC242774
0.8936	High Similarity	NPC18185
0.8936	High Similarity	NPC262911
0.8936	High Similarity	NPC294558
0.8936	High Similarity	NPC70409
0.8923	High Similarity	NPC188022
0.8923	High Similarity	NPC102540
0.8923	High Similarity	NPC17809
0.8923	High Similarity	NPC285040
0.8923	High Similarity	NPC103420
0.8905	High Similarity	NPC475836
0.8897	High Similarity	NPC18189
0.8897	High Similarity	NPC20829
0.8897	High Similarity	NPC262585
0.8889	High Similarity	NPC473018
0.8889	High Similarity	NPC120633
0.8889	High Similarity	NPC59692
0.8889	High Similarity	NPC117048
0.8889	High Similarity	NPC124085
0.8873	High Similarity	NPC329836
0.8865	High Similarity	NPC260397
0.8865	High Similarity	NPC96576
0.8864	High Similarity	NPC274717
0.8857	High Similarity	NPC475492
0.8855	High Similarity	NPC26879
0.8855	High Similarity	NPC50315
0.8855	High Similarity	NPC230479
0.8855	High Similarity	NPC276212
0.8855	High Similarity	NPC283049
0.8846	High Similarity	NPC197351
0.8846	High Similarity	NPC134195
0.8846	High Similarity	NPC86502
0.8846	High Similarity	NPC246648
0.8846	High Similarity	NPC106914
0.8841	High Similarity	NPC22317
0.8841	High Similarity	NPC20520
0.8841	High Similarity	NPC61783
0.8837	High Similarity	NPC150026
0.8832	High Similarity	NPC474687
0.8832	High Similarity	NPC477938
0.8824	High Similarity	NPC258780
0.8824	High Similarity	NPC37410
0.8815	High Similarity	NPC469610
0.8815	High Similarity	NPC77196
0.8811	High Similarity	NPC211561
0.8806	High Similarity	NPC237424
0.8806	High Similarity	NPC472590
0.8806	High Similarity	NPC238168
0.8806	High Similarity	NPC8899
0.8806	High Similarity	NPC162801
0.8797	High Similarity	NPC134360
0.8794	High Similarity	NPC469557
0.8794	High Similarity	NPC181615
0.8788	High Similarity	NPC149796
0.8779	High Similarity	NPC81641
0.8779	High Similarity	NPC113495
0.8777	High Similarity	NPC178054
0.8777	High Similarity	NPC5155
0.8777	High Similarity	NPC263261
0.8777	High Similarity	NPC87725
0.8769	High Similarity	NPC38761
0.8769	High Similarity	NPC76465
0.8767	High Similarity	NPC157333
0.876	High Similarity	NPC193364
0.876	High Similarity	NPC54972
0.876	High Similarity	NPC476633
0.8759	High Similarity	NPC476391
0.8759	High Similarity	NPC170328
0.8759	High Similarity	NPC472647
0.8759	High Similarity	NPC191462
0.8759	High Similarity	NPC472648
0.8759	High Similarity	NPC3049
0.8759	High Similarity	NPC472649
0.8759	High Similarity	NPC133463
0.8759	High Similarity	NPC206525
0.875	High Similarity	NPC66840
0.875	High Similarity	NPC256307
0.875	High Similarity	NPC477612
0.8741	High Similarity	NPC469611
0.8732	High Similarity	NPC102280
0.8732	High Similarity	NPC248053
0.8732	High Similarity	NPC155564
0.8723	High Similarity	NPC12641
0.8723	High Similarity	NPC93323
0.8723	High Similarity	NPC45257
0.8723	High Similarity	NPC280092
0.8707	High Similarity	NPC202104
0.8705	High Similarity	NPC27495
0.8705	High Similarity	NPC309124
0.8705	High Similarity	NPC184797
0.8702	High Similarity	NPC256015
0.8702	High Similarity	NPC294156
0.8696	High Similarity	NPC71465
0.8696	High Similarity	NPC474390
0.8696	High Similarity	NPC472646
0.8692	High Similarity	NPC36016
0.8692	High Similarity	NPC100099
0.869	High Similarity	NPC321972
0.869	High Similarity	NPC324517
0.869	High Similarity	NPC329343
0.8686	High Similarity	NPC473413
0.8676	High Similarity	NPC92805
0.8671	High Similarity	NPC16269

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 NPC125579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	948
0.2-0.3	1604
0.3-0.4	2717
0.4-0.5	1717
0.5-0.6	1017
0.6-0.7	614
0.7-0.8	119
0.8-0.85	9
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9308	High Similarity	NPD4907	Clinical (unspecified phase)
0.9154	High Similarity	NPD4908	Phase 1
0.876	High Similarity	NPD1610	Phase 2
0.8507	High Similarity	NPD2861	Phase 2
0.845	Intermediate Similarity	NPD1548	Phase 1
0.8382	Intermediate Similarity	NPD4625	Phase 3
0.8333	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD4749	Approved
0.8188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3027	Phase 3
0.7974	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7768	Phase 2
0.7905	Intermediate Similarity	NPD7212	Phase 2
0.7905	Intermediate Similarity	NPD7213	Phase 3
0.7887	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD5124	Phase 1
0.7852	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD7447	Phase 1
0.7834	Intermediate Similarity	NPD6959	Discontinued
0.7823	Intermediate Similarity	NPD7466	Approved
0.7817	Intermediate Similarity	NPD4060	Phase 1
0.781	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD7037	Approved
0.777	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD3892	Phase 2
0.7677	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7229	Phase 3
0.7643	Intermediate Similarity	NPD6584	Phase 3
0.7619	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3750	Approved
0.758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1549	Phase 2
0.7554	Intermediate Similarity	NPD5327	Phase 3
0.7551	Intermediate Similarity	NPD6100	Approved
0.7551	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD7041	Phase 2
0.755	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7411	Suspended
0.7536	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD8651	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD6696	Suspended
0.7484	Intermediate Similarity	NPD4380	Phase 2
0.7484	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD5588	Approved
0.7468	Intermediate Similarity	NPD4965	Approved
0.7468	Intermediate Similarity	NPD4966	Approved
0.7468	Intermediate Similarity	NPD4967	Phase 2
0.7467	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4097	Suspended
0.7452	Intermediate Similarity	NPD8455	Phase 2
0.7452	Intermediate Similarity	NPD7819	Suspended
0.7448	Intermediate Similarity	NPD4140	Approved
0.7439	Intermediate Similarity	NPD5844	Phase 1
0.7438	Intermediate Similarity	NPD5494	Approved
0.7436	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6583	Phase 3
0.7429	Intermediate Similarity	NPD6582	Phase 2
0.7421	Intermediate Similarity	NPD3749	Approved
0.7419	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6671	Approved
0.7407	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6674	Discontinued
0.74	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1934	Approved
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7362	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6166	Phase 2
0.7362	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4750	Phase 3
0.7347	Intermediate Similarity	NPD6353	Approved
0.7343	Intermediate Similarity	NPD3018	Phase 2
0.7315	Intermediate Similarity	NPD2796	Approved
0.7312	Intermediate Similarity	NPD7075	Discontinued
0.731	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6798	Discontinued
0.7305	Intermediate Similarity	NPD6559	Discontinued
0.7297	Intermediate Similarity	NPD4536	Approved
0.7297	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4538	Approved
0.7286	Intermediate Similarity	NPD1091	Approved
0.7279	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD6004	Phase 3
0.7267	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD6002	Phase 3
0.7267	Intermediate Similarity	NPD6005	Phase 3
0.7267	Intermediate Similarity	NPD5763	Approved
0.7267	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5846	Approved
0.7266	Intermediate Similarity	NPD6516	Phase 2
0.7266	Intermediate Similarity	NPD1242	Phase 1
0.7259	Intermediate Similarity	NPD5283	Phase 1
0.7255	Intermediate Similarity	NPD5058	Phase 3
0.7252	Intermediate Similarity	NPD968	Approved
0.725	Intermediate Similarity	NPD3882	Suspended
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7248	Intermediate Similarity	NPD5960	Phase 3
0.7248	Intermediate Similarity	NPD3748	Approved
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2157	Approved
0.7211	Intermediate Similarity	NPD2238	Phase 2
0.7211	Intermediate Similarity	NPD3620	Phase 2
0.7211	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD846	Approved
0.7209	Intermediate Similarity	NPD940	Approved
0.7208	Intermediate Similarity	NPD1511	Approved
0.7205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2797	Approved
0.7185	Intermediate Similarity	NPD5535	Approved
0.7183	Intermediate Similarity	NPD2982	Phase 2
0.7183	Intermediate Similarity	NPD2983	Phase 2
0.7181	Intermediate Similarity	NPD7119	Phase 2
0.7181	Intermediate Similarity	NPD7097	Phase 1
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7161	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7020	Approved
0.7161	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD7019	Approved
0.7161	Intermediate Similarity	NPD2534	Approved
0.7161	Intermediate Similarity	NPD2533	Approved
0.7153	Intermediate Similarity	NPD7157	Approved
0.7153	Intermediate Similarity	NPD4624	Approved
0.7143	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7134	Intermediate Similarity	NPD1653	Approved
0.7133	Intermediate Similarity	NPD3225	Approved
0.7125	Intermediate Similarity	NPD2801	Approved
0.7124	Intermediate Similarity	NPD6331	Phase 2
0.7123	Intermediate Similarity	NPD7095	Approved
0.7122	Intermediate Similarity	NPD7741	Discontinued
0.7122	Intermediate Similarity	NPD3091	Approved
0.7115	Intermediate Similarity	NPD1512	Approved
0.7115	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD2235	Phase 2
0.7113	Intermediate Similarity	NPD1608	Approved
0.7113	Intermediate Similarity	NPD2981	Phase 2
0.7113	Intermediate Similarity	NPD2231	Phase 2
0.7108	Intermediate Similarity	NPD7473	Discontinued
0.7105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1240	Approved
0.7095	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5451	Approved
0.7089	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1551	Phase 2
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7083	Intermediate Similarity	NPD3094	Phase 2
0.7076	Intermediate Similarity	NPD8054	Approved
0.7076	Intermediate Similarity	NPD8053	Approved
0.7075	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD5691	Approved
0.7068	Intermediate Similarity	NPD290	Approved
0.7068	Intermediate Similarity	NPD2342	Discontinued
0.7063	Intermediate Similarity	NPD6801	Discontinued
0.7059	Intermediate Similarity	NPD7843	Approved
0.7059	Intermediate Similarity	NPD2800	Approved
0.7059	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1652	Phase 2
0.7054	Intermediate Similarity	NPD3020	Approved
0.7051	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3092	Approved
0.7039	Intermediate Similarity	NPD7030	Discontinued
0.7037	Intermediate Similarity	NPD7773	Phase 2
0.7034	Intermediate Similarity	NPD3690	Phase 2
0.7034	Intermediate Similarity	NPD3691	Phase 2
0.703	Intermediate Similarity	NPD3787	Discontinued
0.7027	Intermediate Similarity	NPD6233	Phase 2
0.7024	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4108	Discontinued
0.7019	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8312	Approved
0.7018	Intermediate Similarity	NPD8313	Approved
0.7013	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD1182	Approved
0.7	Intermediate Similarity	NPD1607	Approved
0.7	Intermediate Similarity	NPD6072	Discontinued
0.7	Intermediate Similarity	NPD6580	Approved
0.7	Intermediate Similarity	NPD6581	Approved
0.6993	Remote Similarity	NPD1840	Phase 2
0.6993	Remote Similarity	NPD2424	Discontinued
0.6987	Remote Similarity	NPD7390	Discontinued
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)

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