NPASS Compound

Structure

CID226304 OpenBabel06191716022D 36 39 0 0 1 0 0 0 0 0999 V2000 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 2.5981 -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 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 1.7321 0.0000 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 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 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 8 2 0 0 0 0 3 12 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 11 2 0 0 0 0 7 24 1 0 0 0 0 8 21 1 0 0 0 0 9 25 1 0 0 0 0 10 15 2 0 0 0 0 10 26 1 0 0 0 0 11 15 1 0 0 0 0 11 34 1 0 0 0 0 12 16 2 0 0 0 0 12 32 1 0 0 0 0 13 16 1 0 0 0 0 13 33 1 0 0 0 0 14 7 1 6 0 0 0 14 17 1 0 0 0 0 14 35 1 0 0 0 0 15 18 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 28 1 1 0 0 0 18 22 1 0 0 0 0 18 29 2 0 0 0 0 19 20 1 0 0 0 0 19 30 1 6 0 0 0 20 23 1 0 0 0 0 20 31 1 1 0 0 0 21 22 2 0 0 0 0 21 34 1 0 0 0 0 22 36 1 0 0 0 0 23 35 1 0 0 0 0 23 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	508.12
Volume:	465.32
LogP:	0.464
LogD:	0.284
LogS:	-3.855
# Rotatable Bonds:	6
TPSA:	208.74
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.23
Synthetic Accessibility Score:	4.036
Fsp3:	0.348
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.266
MDCK Permeability:	1.774856173142325e-05
Pgp-inhibitor:	0.164
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.682
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	81.1682357788086%
Volume Distribution (VD):	0.933
Pgp-substrate:	23.34905242919922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.745
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.325
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	5.669
Half-life (T1/2):	0.928

ADMET: Toxicity

hERG Blockers:	0.27
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.645
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.392
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.092
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC226304

Natural Product ID:	NPC226304
*Common Name:**	5,7-Dihydroxy-2-(4-Hydroxy-3,5-Dimethoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxychromen-4-One
IUPAC Name:	5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	JMFWYRWPJVEZPV-AVGVHVDKSA-N
Standard InCHI:	InChI=1S/C23H24O13/c1-32-12-3-8(4-13(33-2)16(12)27)21-22(18(29)15-10(26)5-9(25)6-11(15)34-21)36-23-20(31)19(30)17(28)14(7-24)35-23/h3-6,14,17,19-20,23-28,30-31H,7H2,1-2H3/t14-,17-,19+,20-,23+/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1600723
PubChem CID:	5321577
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
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]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19863101]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
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]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
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]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
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]
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]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	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]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	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	n.a.	n.a.	n.a.	Database[HerDing]
NPO5421	Philydrum lanuginosum	Species	Philydraceae	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]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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[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]
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]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14685	Swertia franchetiana	Species	Gentianaceae	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]
NPO5421	Philydrum lanuginosum	Species	Philydraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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]
NPO5421	Philydrum lanuginosum	Species	Philydraceae	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]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17633	Viguiera incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11538	Salvia syriaca	Species	Lamiaceae	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]
NPO4325	Blastochloris viridis	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10417	Ipomoea digitata	Species	Convolvulaceae	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]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	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]
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]
NPO5421	Philydrum lanuginosum	Species	Philydraceae	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]
NPO17865	Amathia pinnata	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8506	Cotyledon secunda	Species	Crassulaceae	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]
NPO15227	Helipterum roseum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10989	Annona cornifolia	Species	Annonaceae	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]
NPO15803	Artemisia assoana	Species	Asteraceae	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]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17786	Marrubium anisodon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3964	Calostephane divaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14395	Lysimachia mauritiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17702	Astragalus sempervirens	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]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6881	Caragana aurantiaca	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]
NPO15467	Hedysarum connatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16089	Dumortiera hirsuta	Species	Dumortieraceae	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]
NPO17544	Acacia adunca	Species	Fabaceae	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]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	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]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17472	Drechslera avenae	Species	Pleosporaceae	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
Potency	3

Activity Type	# Activity
Individual Protein	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[564512]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[564512]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[564512]

☑ 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 NPC226304 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	437
0.1-0.2	1771
0.2-0.3	4055
0.3-0.4	9511
0.4-0.5	8667
0.5-0.6	4310
0.6-0.7	5185
0.7-0.8	5352
0.8-0.85	1634
0.85-0.9	1124
0.9-0.95	452
0.95-1	199

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC325555
1.0	High Similarity	NPC265530
0.9937	High Similarity	NPC120099
0.9937	High Similarity	NPC225434
0.9937	High Similarity	NPC219904
0.9937	High Similarity	NPC203050
0.9937	High Similarity	NPC223747
0.9936	High Similarity	NPC73855
0.9936	High Similarity	NPC328940
0.9936	High Similarity	NPC113968
0.9936	High Similarity	NPC135599
0.9936	High Similarity	NPC277174
0.9874	High Similarity	NPC206123
0.9873	High Similarity	NPC52550
0.9873	High Similarity	NPC19388
0.9873	High Similarity	NPC127546
0.9873	High Similarity	NPC223424
0.9873	High Similarity	NPC240431
0.9873	High Similarity	NPC317489
0.9873	High Similarity	NPC55786
0.9873	High Similarity	NPC173637
0.9873	High Similarity	NPC84362
0.9812	High Similarity	NPC153755
0.981	High Similarity	NPC145038
0.981	High Similarity	NPC281131
0.981	High Similarity	NPC21100
0.981	High Similarity	NPC197285
0.981	High Similarity	NPC88789
0.981	High Similarity	NPC253662
0.981	High Similarity	NPC308404
0.981	High Similarity	NPC118284
0.981	High Similarity	NPC56077
0.981	High Similarity	NPC274618
0.981	High Similarity	NPC276222
0.981	High Similarity	NPC179950
0.9809	High Similarity	NPC222936
0.9809	High Similarity	NPC284960
0.9752	High Similarity	NPC169977
0.9752	High Similarity	NPC4390
0.9752	High Similarity	NPC21666
0.9752	High Similarity	NPC42773
0.9752	High Similarity	NPC24043
0.9752	High Similarity	NPC45522
0.9752	High Similarity	NPC101026
0.975	High Similarity	NPC95866
0.975	High Similarity	NPC116864
0.975	High Similarity	NPC244776
0.9747	High Similarity	NPC22832
0.9747	High Similarity	NPC311830
0.9747	High Similarity	NPC277205
0.9745	High Similarity	NPC473043
0.9691	High Similarity	NPC294815
0.9691	High Similarity	NPC16194
0.9691	High Similarity	NPC476472
0.9691	High Similarity	NPC473327
0.9691	High Similarity	NPC19108
0.9691	High Similarity	NPC220173
0.9689	High Similarity	NPC117260
0.9689	High Similarity	NPC471748
0.9689	High Similarity	NPC175107
0.9689	High Similarity	NPC471725
0.9689	High Similarity	NPC190003
0.9689	High Similarity	NPC155877
0.9689	High Similarity	NPC33054
0.9689	High Similarity	NPC134532
0.9689	High Similarity	NPC60735
0.9689	High Similarity	NPC26230
0.9689	High Similarity	NPC476405
0.9689	High Similarity	NPC176740
0.9689	High Similarity	NPC245452
0.9689	High Similarity	NPC203259
0.9688	High Similarity	NPC52382
0.9688	High Similarity	NPC138927
0.9688	High Similarity	NPC227508
0.9688	High Similarity	NPC270578
0.9684	High Similarity	NPC19709
0.9684	High Similarity	NPC270335
0.9684	High Similarity	NPC309025
0.9684	High Similarity	NPC191306
0.9684	High Similarity	NPC88023
0.9684	High Similarity	NPC243930
0.9632	High Similarity	NPC198324
0.9632	High Similarity	NPC472385
0.9627	High Similarity	NPC20505
0.9627	High Similarity	NPC84265
0.9627	High Similarity	NPC67326
0.9627	High Similarity	NPC285197
0.9627	High Similarity	NPC235260
0.9627	High Similarity	NPC259896
0.9627	High Similarity	NPC245014
0.9627	High Similarity	NPC155763
0.9627	High Similarity	NPC254855
0.9627	High Similarity	NPC255157
0.9627	High Similarity	NPC29958
0.9627	High Similarity	NPC282987
0.9627	High Similarity	NPC156869
0.9627	High Similarity	NPC136042
0.9627	High Similarity	NPC67105
0.9625	High Similarity	NPC229729
0.9625	High Similarity	NPC92565
0.9625	High Similarity	NPC160156
0.9625	High Similarity	NPC275454
0.9623	High Similarity	NPC34531
0.962	High Similarity	NPC77660
0.962	High Similarity	NPC189142
0.9618	High Similarity	NPC110349
0.9573	High Similarity	NPC173837
0.9573	High Similarity	NPC217520
0.9573	High Similarity	NPC139571
0.9573	High Similarity	NPC251417
0.9573	High Similarity	NPC168584
0.9573	High Similarity	NPC89052
0.9571	High Similarity	NPC115760
0.9571	High Similarity	NPC294629
0.9571	High Similarity	NPC237435
0.9571	High Similarity	NPC264735
0.9571	High Similarity	NPC49344
0.9571	High Similarity	NPC135277
0.9571	High Similarity	NPC43211
0.9571	High Similarity	NPC210094
0.9571	High Similarity	NPC101191
0.9571	High Similarity	NPC477848
0.9565	High Similarity	NPC201292
0.9565	High Similarity	NPC209296
0.9565	High Similarity	NPC58053
0.9565	High Similarity	NPC475942
0.9565	High Similarity	NPC476771
0.9565	High Similarity	NPC186807
0.9565	High Similarity	NPC195257
0.9565	High Similarity	NPC93337
0.9565	High Similarity	NPC226294
0.9565	High Similarity	NPC105025
0.9565	High Similarity	NPC469931
0.9565	High Similarity	NPC45638
0.9563	High Similarity	NPC5778
0.9563	High Similarity	NPC115674
0.9563	High Similarity	NPC255615
0.9563	High Similarity	NPC254306
0.9563	High Similarity	NPC67037
0.9563	High Similarity	NPC236934
0.9563	High Similarity	NPC210073
0.956	High Similarity	NPC168822
0.9557	High Similarity	NPC182045
0.9515	High Similarity	NPC126784
0.9515	High Similarity	NPC470443
0.9515	High Similarity	NPC473571
0.9515	High Similarity	NPC192539
0.9515	High Similarity	NPC470444
0.9515	High Similarity	NPC110941
0.9515	High Similarity	NPC241423
0.9515	High Similarity	NPC473682
0.9512	High Similarity	NPC292019
0.9512	High Similarity	NPC202908
0.9512	High Similarity	NPC169733
0.9512	High Similarity	NPC89127
0.9512	High Similarity	NPC122467
0.9512	High Similarity	NPC65563
0.9512	High Similarity	NPC48984
0.9512	High Similarity	NPC233994
0.9512	High Similarity	NPC211532
0.9512	High Similarity	NPC8573
0.9512	High Similarity	NPC219043
0.9512	High Similarity	NPC14187
0.9512	High Similarity	NPC470949
0.9512	High Similarity	NPC471669
0.9506	High Similarity	NPC231194
0.9506	High Similarity	NPC51326
0.9506	High Similarity	NPC224462
0.9506	High Similarity	NPC72249
0.9503	High Similarity	NPC477502
0.9503	High Similarity	NPC48640
0.9503	High Similarity	NPC58716
0.9503	High Similarity	NPC146792
0.9503	High Similarity	NPC149244
0.9503	High Similarity	NPC45618
0.9497	High Similarity	NPC127782
0.9497	High Similarity	NPC300537
0.9458	High Similarity	NPC473073
0.9458	High Similarity	NPC473071
0.9455	High Similarity	NPC258044
0.9455	High Similarity	NPC196127
0.9455	High Similarity	NPC35167
0.9455	High Similarity	NPC267680
0.9455	High Similarity	NPC293626
0.9455	High Similarity	NPC477895
0.9455	High Similarity	NPC217387
0.9451	High Similarity	NPC253685
0.9451	High Similarity	NPC223426
0.9451	High Similarity	NPC81042
0.9451	High Similarity	NPC214621
0.9451	High Similarity	NPC34267
0.9448	High Similarity	NPC254540
0.9448	High Similarity	NPC48773
0.9448	High Similarity	NPC205076
0.9448	High Similarity	NPC256760
0.9448	High Similarity	NPC235575
0.9448	High Similarity	NPC211594
0.9448	High Similarity	NPC172807
0.9448	High Similarity	NPC307518
0.9448	High Similarity	NPC476772

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 NPC226304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	955
0.2-0.3	1992
0.3-0.4	2671
0.4-0.5	1791
0.5-0.6	893
0.6-0.7	292
0.7-0.8	127
0.8-0.85	12
0.85-0.9	18
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9689	High Similarity	NPD6797	Phase 2
0.963	High Similarity	NPD7251	Discontinued
0.9571	High Similarity	NPD4338	Clinical (unspecified phase)
0.9571	High Similarity	NPD7808	Phase 3
0.9565	High Similarity	NPD7054	Approved
0.9506	High Similarity	NPD7472	Approved
0.9387	High Similarity	NPD7074	Phase 3
0.9264	High Similarity	NPD3818	Discontinued
0.9141	High Similarity	NPD6168	Clinical (unspecified phase)
0.9141	High Similarity	NPD6166	Phase 2
0.9141	High Similarity	NPD6167	Clinical (unspecified phase)
0.9125	High Similarity	NPD4381	Clinical (unspecified phase)
0.9091	High Similarity	NPD7804	Clinical (unspecified phase)
0.9	High Similarity	NPD3817	Phase 2
0.8994	High Similarity	NPD1934	Approved
0.8827	High Similarity	NPD3882	Suspended
0.882	High Similarity	NPD2801	Approved
0.882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8734	High Similarity	NPD1512	Approved
0.8608	High Similarity	NPD1511	Approved
0.8598	High Similarity	NPD4868	Clinical (unspecified phase)
0.8545	High Similarity	NPD7075	Discontinued
0.8519	High Similarity	NPD4380	Phase 2
0.843	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD5402	Approved
0.8415	Intermediate Similarity	NPD6801	Discontinued
0.8382	Intermediate Similarity	NPD6559	Discontinued
0.8364	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5403	Approved
0.8323	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6799	Approved
0.821	Intermediate Similarity	NPD5401	Approved
0.8171	Intermediate Similarity	NPD1653	Approved
0.8118	Intermediate Similarity	NPD5494	Approved
0.8113	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1549	Phase 2
0.8046	Intermediate Similarity	NPD3751	Discontinued
0.8036	Intermediate Similarity	NPD1465	Phase 2
0.8023	Intermediate Similarity	NPD3787	Discontinued
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD7685	Pre-registration
0.7965	Intermediate Similarity	NPD6959	Discontinued
0.7964	Intermediate Similarity	NPD6599	Discontinued
0.7943	Intermediate Similarity	NPD7228	Approved
0.7937	Intermediate Similarity	NPD2796	Approved
0.7929	Intermediate Similarity	NPD7819	Suspended
0.7919	Intermediate Similarity	NPD6232	Discontinued
0.7917	Intermediate Similarity	NPD7411	Suspended
0.7892	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7473	Discontinued
0.7879	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD1510	Phase 2
0.7861	Intermediate Similarity	NPD7199	Phase 2
0.7849	Intermediate Similarity	NPD6234	Discontinued
0.7849	Intermediate Similarity	NPD919	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD37	Approved
0.7759	Intermediate Similarity	NPD1247	Approved
0.7736	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1613	Approved
0.7733	Intermediate Similarity	NPD4965	Approved
0.7733	Intermediate Similarity	NPD4966	Approved
0.7733	Intermediate Similarity	NPD4967	Phase 2
0.773	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6190	Approved
0.768	Intermediate Similarity	NPD8312	Approved
0.768	Intermediate Similarity	NPD8313	Approved
0.7672	Intermediate Similarity	NPD6778	Approved
0.7672	Intermediate Similarity	NPD6776	Approved
0.7672	Intermediate Similarity	NPD6777	Approved
0.7672	Intermediate Similarity	NPD6779	Approved
0.7672	Intermediate Similarity	NPD6781	Approved
0.7672	Intermediate Similarity	NPD6780	Approved
0.7672	Intermediate Similarity	NPD6782	Approved
0.767	Intermediate Similarity	NPD3926	Phase 2
0.7669	Intermediate Similarity	NPD7266	Discontinued
0.7663	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7435	Discontinued
0.7636	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1240	Approved
0.7617	Intermediate Similarity	NPD7584	Approved
0.7605	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD230	Phase 1
0.7578	Intermediate Similarity	NPD1933	Approved
0.7547	Intermediate Similarity	NPD3027	Phase 3
0.7538	Intermediate Similarity	NPD8151	Discontinued
0.7532	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1607	Approved
0.753	Intermediate Similarity	NPD3750	Approved
0.7516	Intermediate Similarity	NPD943	Approved
0.7513	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7240	Approved
0.7461	Intermediate Similarity	NPD7698	Approved
0.7461	Intermediate Similarity	NPD7696	Phase 3
0.7461	Intermediate Similarity	NPD7697	Approved
0.7429	Intermediate Similarity	NPD7768	Phase 2
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD7870	Phase 2
0.7423	Intermediate Similarity	NPD7871	Phase 2
0.7414	Intermediate Similarity	NPD8455	Phase 2
0.7411	Intermediate Similarity	NPD7874	Approved
0.7411	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6534	Approved
0.7407	Intermediate Similarity	NPD6535	Approved
0.7398	Intermediate Similarity	NPD7701	Phase 2
0.7394	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3749	Approved
0.7362	Intermediate Similarity	NPD447	Suspended
0.7353	Intermediate Similarity	NPD2533	Approved
0.7353	Intermediate Similarity	NPD2534	Approved
0.7353	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7700	Phase 2
0.7292	Intermediate Similarity	NPD7699	Phase 2
0.7289	Intermediate Similarity	NPD2935	Discontinued
0.7286	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7783	Phase 2
0.7286	Intermediate Similarity	NPD7801	Approved
0.7262	Intermediate Similarity	NPD6674	Discontinued
0.7262	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2800	Approved
0.7245	Intermediate Similarity	NPD8320	Phase 1
0.7245	Intermediate Similarity	NPD8319	Approved
0.7238	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6823	Phase 2
0.7229	Intermediate Similarity	NPD3748	Approved
0.7222	Intermediate Similarity	NPD7585	Approved
0.7216	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6099	Approved
0.7186	Intermediate Similarity	NPD6100	Approved
0.7181	Intermediate Similarity	NPD8150	Discontinued
0.7181	Intermediate Similarity	NPD8434	Phase 2
0.7178	Intermediate Similarity	NPD6798	Discontinued
0.7172	Intermediate Similarity	NPD7583	Approved
0.7168	Intermediate Similarity	NPD920	Approved
0.7165	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1243	Approved
0.7152	Intermediate Similarity	NPD1091	Approved
0.7151	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD5953	Discontinued
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.7108	Intermediate Similarity	NPD6651	Approved
0.7099	Intermediate Similarity	NPD9494	Approved
0.7093	Intermediate Similarity	NPD7390	Discontinued
0.7086	Intermediate Similarity	NPD3226	Approved
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7079	Intermediate Similarity	NPD5353	Approved
0.7067	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6844	Discontinued
0.7059	Intermediate Similarity	NPD1652	Phase 2
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.7055	Intermediate Similarity	NPD4908	Phase 1
0.7053	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD2798	Approved
0.7035	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7286	Phase 2
0.702	Intermediate Similarity	NPD7680	Approved
0.7018	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6213	Phase 3
0.6995	Remote Similarity	NPD6212	Phase 3
0.6975	Remote Similarity	NPD1203	Approved
0.6973	Remote Similarity	NPD2163	Approved
0.697	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2313	Discontinued
0.6963	Remote Similarity	NPD6841	Approved
0.6963	Remote Similarity	NPD6843	Phase 3
0.6963	Remote Similarity	NPD6842	Approved
0.6957	Remote Similarity	NPD2403	Approved
0.6954	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5124	Phase 1
0.6946	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2344	Approved
0.6941	Remote Similarity	NPD2346	Discontinued
0.694	Remote Similarity	NPD5711	Approved
0.694	Remote Similarity	NPD5710	Approved
0.6937	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5242	Approved
0.6899	Remote Similarity	NPD1548	Phase 1
0.6895	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD9269	Phase 2
0.6893	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4060	Phase 1

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