NPASS Compound

Structure

CID233467 OpenBabel06191716032D 45 50 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 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 -7.3690 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3690 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3690 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3690 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5683 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9211 -3.5032 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 -6.2082 -4.6622 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 1.7321 0.0000 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 -6.8690 -1.0000 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 -5.5902 -2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8774 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2301 -4.4543 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 -4.3301 -0.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 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 0.0000 -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 -5.8690 -1.0000 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 -2.5981 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8690 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8555 -4.1270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5610 -5.1974 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 -5.2812 -0.1910 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 4 2 0 0 0 0 1 17 1 0 0 0 0 2 7 1 0 0 0 0 2 17 2 0 0 0 0 3 8 2 0 0 0 0 3 17 1 0 0 0 0 4 19 1 0 0 0 0 5 9 1 0 0 0 0 5 18 2 0 0 0 0 6 10 2 0 0 0 0 6 18 1 0 0 0 0 7 21 2 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 22 1 0 0 0 0 11 20 2 0 0 0 0 11 23 1 0 0 0 0 12 20 1 0 0 0 0 12 24 2 0 0 0 0 13 19 2 0 0 0 0 13 25 1 0 0 0 0 14 23 2 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 15 26 1 0 0 0 0 16 35 1 0 0 0 0 19 28 1 0 0 0 0 21 36 1 0 0 0 0 22 37 1 0 0 0 0 23 38 1 0 0 0 0 24 39 1 0 0 0 0 25 43 1 0 0 0 0 26 28 2 0 0 0 0 26 44 1 0 0 0 0 27 16 1 6 0 0 0 27 30 1 0 0 0 0 27 45 1 0 0 0 0 28 29 1 0 0 0 0 29 20 1 6 0 0 0 29 33 1 0 0 0 0 30 31 1 0 0 0 0 30 40 1 1 0 0 0 31 32 1 0 0 0 0 31 41 1 6 0 0 0 32 34 1 0 0 0 0 32 42 1 1 0 0 0 33 18 1 1 0 0 0 33 44 1 0 0 0 0 34 43 1 6 0 0 0 34 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.19
Volume:	607.7
LogP:	3.125
LogD:	2.92
LogS:	-4.08
# Rotatable Bonds:	7
TPSA:	189.53
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	4.524
Fsp3:	0.235
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.434
MDCK Permeability:	7.883360012783669e-06
Pgp-inhibitor:	0.047
Pgp-substrate:	0.801
Human Intestinal Absorption (HIA):	0.52
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	98.7044906616211%
Volume Distribution (VD):	0.528
Pgp-substrate:	1.8982365131378174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.178
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.732
CYP2C9-substrate:	0.972
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.73
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	9.853
Half-life (T1/2):	0.535

ADMET: Toxicity

hERG Blockers:	0.307
Human Hepatotoxicity (H-HT):	0.383
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.079
Skin Sensitization:	0.952
Carcinogencity:	0.222
Eye Corrosion:	0.003
Eye Irritation:	0.156
Respiratory Toxicity:	0.046

Download Data

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

Natural Product: NPC233467

Natural Product ID:	NPC233467
*Common Name:**	Epsilon-Viniferin Glucoside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(2S,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Epsilon-Viniferin Glucoside
Standard InCHIKey:	NHYFNLFVNSLRES-YNVKLIFMSA-N
Standard InCHI:	InChI=1S/C34H32O11/c35-16-27-30(40)31(41)32(42)34(45-27)43-25-13-19(4-1-17-2-7-21(36)8-3-17)28-26(15-25)44-33(18-5-9-22(37)10-6-18)29(28)20-11-23(38)14-24(39)12-20/h1-15,27,29-42H,16H2/b4-1+/t27-,29+,30-,31+,32-,33-,34-/m1/s1
SMILES:	C(=Cc1cc(cc2c1[C@H](c1cc(cc(c1)O)O)[C@@H](c1ccc(cc1)O)O2)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1082598
PubChem CID:	46890010
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]
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]
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]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
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]
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]
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[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]
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]
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]
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]
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]
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]
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]
NPO6881	Caragana aurantiaca	Species	Fabaceae	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]
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]
NPO17544	Acacia adunca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO7562	Premna odorata	Species	Lamiaceae	Eukaryota	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]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	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]
NPO11917	Asterospicularia laurae	Species	Xeniidae	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]
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]
NPO17633	Viguiera incana	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]
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]
NPO16369	Lepisorus ussuriensis	Species	Polypodiaceae	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]
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]
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]
NPO17942	Wikstroemia retusa	Species	Thymelaeaceae	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]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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]
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]
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]
NPO16731	Phoebe pittieri	Species	Lauraceae	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
EC50	1
IC50	1
Others	9

Activity Type	# Activity
Cell Line	3
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	80.0	%	PMID[463235]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	79.0	%	PMID[463235]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	87.0	%	PMID[463235]
NPT2	Others	Unspecified		Inhibition	=	93.0	%	PMID[463234]
NPT2	Others	Unspecified		EC50	=	200.0	nM	PMID[463234]
NPT2	Others	Unspecified		IC50	<	1000.0	nM	PMID[463235]
NPT2	Others	Unspecified		Inhibition	=	59.0	%	PMID[463235]
NPT2	Others	Unspecified		Inhibition	=	93.0	%	PMID[463235]
NPT2	Others	Unspecified		Inhibition	=	97.0	%	PMID[463235]
NPT2	Others	Unspecified		Inhibition	=	70.0	%	PMID[463235]
NPT2	Others	Unspecified		Inhibition	=	89.0	%	PMID[463235]

☑ 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 NPC233467 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	489
0.1-0.2	1631
0.2-0.3	4021
0.3-0.4	9807
0.4-0.5	8487
0.5-0.6	5005
0.6-0.7	7811
0.7-0.8	4528
0.8-0.85	645
0.85-0.9	250
0.9-0.95	18
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC59692
0.9474	High Similarity	NPC48880
0.9281	High Similarity	NPC100936
0.9281	High Similarity	NPC1253
0.9262	High Similarity	NPC259707
0.9091	High Similarity	NPC185231
0.9054	High Similarity	NPC248053
0.9054	High Similarity	NPC155564
0.9054	High Similarity	NPC102280
0.9041	High Similarity	NPC472353
0.9007	High Similarity	NPC471403
0.8973	High Similarity	NPC108674
0.8947	High Similarity	NPC44192
0.8947	High Similarity	NPC226108
0.8947	High Similarity	NPC322899
0.8947	High Similarity	NPC272552
0.8947	High Similarity	NPC134911
0.8947	High Similarity	NPC46283
0.8947	High Similarity	NPC469944
0.8933	High Similarity	NPC227516
0.8933	High Similarity	NPC20757
0.8919	High Similarity	NPC15659
0.8919	High Similarity	NPC304894
0.8904	High Similarity	NPC174787
0.8904	High Similarity	NPC213607
0.8904	High Similarity	NPC182509
0.8903	High Similarity	NPC4809
0.8903	High Similarity	NPC73517
0.8903	High Similarity	NPC147743
0.8889	High Similarity	NPC20050
0.8889	High Similarity	NPC15109
0.8889	High Similarity	NPC11727
0.8889	High Similarity	NPC306267
0.8867	High Similarity	NPC39657
0.8859	High Similarity	NPC149633
0.8851	High Similarity	NPC163508
0.8851	High Similarity	NPC173203
0.8846	High Similarity	NPC205613
0.8846	High Similarity	NPC151474
0.8846	High Similarity	NPC471404
0.8846	High Similarity	NPC86630
0.8846	High Similarity	NPC159526
0.8846	High Similarity	NPC106601
0.8846	High Similarity	NPC212614
0.8844	High Similarity	NPC277331
0.8844	High Similarity	NPC210192
0.8844	High Similarity	NPC100482
0.8831	High Similarity	NPC157333
0.8824	High Similarity	NPC21902
0.8816	High Similarity	NPC472709
0.8816	High Similarity	NPC185955
0.8816	High Similarity	NPC225815
0.8816	High Similarity	NPC260781
0.8816	High Similarity	NPC214326
0.8816	High Similarity	NPC469706
0.8816	High Similarity	NPC218041
0.8816	High Similarity	NPC472710
0.8816	High Similarity	NPC477612
0.8816	High Similarity	NPC182368
0.8816	High Similarity	NPC9933
0.8816	High Similarity	NPC145979
0.8816	High Similarity	NPC469707
0.8808	High Similarity	NPC270751
0.8808	High Similarity	NPC329836
0.8808	High Similarity	NPC280945
0.8792	High Similarity	NPC469313
0.8792	High Similarity	NPC138227
0.8792	High Similarity	NPC168579
0.8792	High Similarity	NPC151704
0.8792	High Similarity	NPC76176
0.8767	High Similarity	NPC262328
0.8767	High Similarity	NPC87777
0.8758	High Similarity	NPC321972
0.8758	High Similarity	NPC473621
0.8758	High Similarity	NPC329343
0.8758	High Similarity	NPC324517
0.875	High Similarity	NPC286235
0.875	High Similarity	NPC321657
0.875	High Similarity	NPC470208
0.875	High Similarity	NPC295573
0.875	High Similarity	NPC318373
0.875	High Similarity	NPC476969
0.875	High Similarity	NPC55158
0.875	High Similarity	NPC59516
0.875	High Similarity	NPC51328
0.8742	High Similarity	NPC202742
0.8742	High Similarity	NPC237546
0.8742	High Similarity	NPC224921
0.8742	High Similarity	NPC236202
0.8742	High Similarity	NPC204770
0.8742	High Similarity	NPC262911
0.8742	High Similarity	NPC294558
0.8742	High Similarity	NPC231712
0.8742	High Similarity	NPC112819
0.8742	High Similarity	NPC58190
0.8742	High Similarity	NPC111134
0.8742	High Similarity	NPC263940
0.8742	High Similarity	NPC70409
0.8742	High Similarity	NPC242774
0.8742	High Similarity	NPC6702
0.8742	High Similarity	NPC15538
0.8742	High Similarity	NPC153182
0.8742	High Similarity	NPC18185
0.8742	High Similarity	NPC82917
0.8742	High Similarity	NPC174251
0.8742	High Similarity	NPC473480
0.8742	High Similarity	NPC108811
0.8742	High Similarity	NPC133209
0.8742	High Similarity	NPC170103
0.8733	High Similarity	NPC271076
0.8733	High Similarity	NPC475096
0.8733	High Similarity	NPC23807
0.8725	High Similarity	NPC37793
0.8716	High Similarity	NPC257095
0.8716	High Similarity	NPC89686
0.8716	High Similarity	NPC273932
0.8716	High Similarity	NPC178054
0.8701	High Similarity	NPC474442
0.8701	High Similarity	NPC279406
0.8701	High Similarity	NPC226809
0.8699	High Similarity	NPC40664
0.8699	High Similarity	NPC3293
0.8699	High Similarity	NPC197723
0.8699	High Similarity	NPC165482
0.8699	High Similarity	NPC141717
0.8699	High Similarity	NPC138350
0.8693	High Similarity	NPC238140
0.869	High Similarity	NPC130496
0.869	High Similarity	NPC188555
0.8684	High Similarity	NPC130449
0.8684	High Similarity	NPC304048
0.8684	High Similarity	NPC226153
0.8684	High Similarity	NPC248132
0.8681	High Similarity	NPC26080
0.8681	High Similarity	NPC165686
0.8681	High Similarity	NPC85799
0.8681	High Similarity	NPC303422
0.8675	High Similarity	NPC274454
0.8675	High Similarity	NPC96576
0.8675	High Similarity	NPC93610
0.8675	High Similarity	NPC125755
0.8675	High Similarity	NPC190714
0.8675	High Similarity	NPC71686
0.8675	High Similarity	NPC14468
0.8675	High Similarity	NPC176804
0.8675	High Similarity	NPC215678
0.8675	High Similarity	NPC99515
0.8675	High Similarity	NPC241846
0.8667	High Similarity	NPC225445
0.8667	High Similarity	NPC473046
0.8667	High Similarity	NPC472155
0.8667	High Similarity	NPC28440
0.8667	High Similarity	NPC472712
0.8667	High Similarity	NPC472713
0.8667	High Similarity	NPC187774
0.8667	High Similarity	NPC171932
0.8667	High Similarity	NPC475492
0.8667	High Similarity	NPC118385
0.8654	High Similarity	NPC202104
0.8649	High Similarity	NPC193920
0.8645	High Similarity	NPC224161
0.8645	High Similarity	NPC78809
0.8639	High Similarity	NPC470308
0.8639	High Similarity	NPC470307
0.8639	High Similarity	NPC134260
0.863	High Similarity	NPC238243
0.863	High Similarity	NPC125579
0.8627	High Similarity	NPC473266
0.8627	High Similarity	NPC95392
0.8627	High Similarity	NPC211561
0.8627	High Similarity	NPC55715
0.8627	High Similarity	NPC107862
0.8627	High Similarity	NPC177172
0.8627	High Similarity	NPC180605
0.8627	High Similarity	NPC470098
0.8627	High Similarity	NPC470826
0.8627	High Similarity	NPC44452
0.8627	High Similarity	NPC122980
0.8627	High Similarity	NPC148516
0.8627	High Similarity	NPC35877
0.8621	High Similarity	NPC115022
0.8621	High Similarity	NPC294166
0.8618	High Similarity	NPC114505
0.8618	High Similarity	NPC327412
0.8618	High Similarity	NPC320970
0.8618	High Similarity	NPC193473
0.8618	High Similarity	NPC31325
0.8618	High Similarity	NPC15956
0.8618	High Similarity	NPC224674
0.8618	High Similarity	NPC213074
0.8618	High Similarity	NPC328567
0.8618	High Similarity	NPC320671
0.8618	High Similarity	NPC99183
0.8618	High Similarity	NPC275284
0.8618	High Similarity	NPC227902
0.8611	High Similarity	NPC121376
0.8609	High Similarity	NPC181615
0.8609	High Similarity	NPC476301
0.8609	High Similarity	NPC277867
0.8609	High Similarity	NPC43508

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 NPC233467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	847
0.2-0.3	1852
0.3-0.4	2767
0.4-0.5	1704
0.5-0.6	995
0.6-0.7	506
0.7-0.8	79
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8276	Intermediate Similarity	NPD4908	Phase 1
0.8242	Intermediate Similarity	NPD7228	Approved
0.8239	Intermediate Similarity	NPD8455	Phase 2
0.8176	Intermediate Similarity	NPD1613	Approved
0.8176	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6674	Discontinued
0.8049	Intermediate Similarity	NPD7199	Phase 2
0.7953	Intermediate Similarity	NPD8312	Approved
0.7953	Intermediate Similarity	NPD8313	Approved
0.795	Intermediate Similarity	NPD37	Approved
0.7927	Intermediate Similarity	NPD6234	Discontinued
0.7917	Intermediate Similarity	NPD1610	Phase 2
0.7917	Intermediate Similarity	NPD1091	Approved
0.7914	Intermediate Similarity	NPD4967	Phase 2
0.7914	Intermediate Similarity	NPD4966	Approved
0.7914	Intermediate Similarity	NPD4965	Approved
0.7905	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2861	Phase 2
0.7838	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7240	Approved
0.7824	Intermediate Similarity	NPD7074	Phase 3
0.7812	Intermediate Similarity	NPD1653	Approved
0.7765	Intermediate Similarity	NPD7054	Approved
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6559	Discontinued
0.7733	Intermediate Similarity	NPD3027	Phase 3
0.7719	Intermediate Similarity	NPD7472	Approved
0.7706	Intermediate Similarity	NPD3818	Discontinued
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7679	Intermediate Similarity	NPD3787	Discontinued
0.763	Intermediate Similarity	NPD7251	Discontinued
0.7616	Intermediate Similarity	NPD4625	Phase 3
0.759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6797	Phase 2
0.7566	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD7266	Discontinued
0.7515	Intermediate Similarity	NPD6959	Discontinued
0.7514	Intermediate Similarity	NPD7680	Approved
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.745	Intermediate Similarity	NPD4749	Approved
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7097	Phase 1
0.7425	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7447	Phase 1
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7391	Intermediate Similarity	NPD5058	Phase 3
0.7391	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5844	Phase 1
0.7346	Intermediate Similarity	NPD7213	Phase 3
0.7346	Intermediate Similarity	NPD7212	Phase 2
0.7315	Intermediate Similarity	NPD3705	Approved
0.7308	Intermediate Similarity	NPD5735	Approved
0.7303	Intermediate Similarity	NPD8053	Approved
0.7303	Intermediate Similarity	NPD8054	Approved
0.7296	Intermediate Similarity	NPD5762	Approved
0.7296	Intermediate Similarity	NPD5763	Approved
0.7289	Intermediate Similarity	NPD4380	Phase 2
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD3892	Phase 2
0.7267	Intermediate Similarity	NPD7466	Approved
0.7267	Intermediate Similarity	NPD7229	Phase 3
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7819	Suspended
0.7202	Intermediate Similarity	NPD1934	Approved
0.7197	Intermediate Similarity	NPD5124	Phase 1
0.7197	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5125	Phase 3
0.7181	Intermediate Similarity	NPD5126	Approved
0.7171	Intermediate Similarity	NPD8651	Approved
0.717	Intermediate Similarity	NPD5588	Approved
0.716	Intermediate Similarity	NPD3750	Approved
0.716	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7037	Approved
0.7135	Intermediate Similarity	NPD7075	Discontinued
0.7135	Intermediate Similarity	NPD3749	Approved
0.7135	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7125	Intermediate Similarity	NPD6100	Approved
0.7125	Intermediate Similarity	NPD6099	Approved
0.7115	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7843	Approved
0.7099	Intermediate Similarity	NPD1652	Phase 2
0.7091	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7075	Intermediate Similarity	NPD7157	Approved
0.7063	Intermediate Similarity	NPD4108	Discontinued
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7062	Intermediate Similarity	NPD8156	Discontinued
0.7059	Intermediate Similarity	NPD1465	Phase 2
0.7045	Intermediate Similarity	NPD7473	Discontinued
0.7039	Intermediate Similarity	NPD7685	Pre-registration
0.703	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7041	Phase 2
0.7025	Intermediate Similarity	NPD3620	Phase 2
0.7025	Intermediate Similarity	NPD4140	Approved
0.7025	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5402	Approved
0.7017	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7870	Phase 2
0.7016	Intermediate Similarity	NPD7871	Phase 2
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD8099	Discontinued
0.7006	Intermediate Similarity	NPD8251	Approved
0.7006	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8252	Approved
0.7	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD6823	Phase 2
0.7	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4536	Approved
0.7	Intermediate Similarity	NPD7119	Phase 2
0.7	Intermediate Similarity	NPD4538	Approved
0.6995	Remote Similarity	NPD6841	Approved
0.6995	Remote Similarity	NPD6842	Approved
0.6995	Remote Similarity	NPD6843	Phase 3
0.6995	Remote Similarity	NPD7906	Approved
0.6993	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5327	Phase 3
0.6988	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6779	Approved
0.6984	Remote Similarity	NPD6777	Approved
0.6984	Remote Similarity	NPD6781	Approved
0.6984	Remote Similarity	NPD6776	Approved
0.6984	Remote Similarity	NPD6782	Approved
0.6984	Remote Similarity	NPD6780	Approved
0.6984	Remote Similarity	NPD6778	Approved
0.6975	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6232	Discontinued
0.6963	Remote Similarity	NPD7697	Approved
0.6963	Remote Similarity	NPD7696	Phase 3
0.6963	Remote Similarity	NPD7698	Approved
0.6963	Remote Similarity	NPD7435	Discontinued
0.6959	Remote Similarity	NPD6671	Approved
0.6959	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5960	Phase 3
0.6954	Remote Similarity	NPD6516	Phase 2
0.6954	Remote Similarity	NPD5846	Approved
0.6954	Remote Similarity	NPD5494	Approved
0.6951	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6696	Suspended
0.6943	Remote Similarity	NPD7095	Approved
0.6941	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7411	Suspended
0.694	Remote Similarity	NPD4663	Approved
0.6933	Remote Similarity	NPD1549	Phase 2
0.6923	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3018	Phase 2
0.6909	Remote Similarity	NPD2677	Approved
0.6907	Remote Similarity	NPD7701	Phase 2
0.6905	Remote Similarity	NPD5403	Approved
0.6903	Remote Similarity	NPD3094	Phase 2
0.6894	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7801	Approved
0.6887	Remote Similarity	NPD1357	Approved
0.6879	Remote Similarity	NPD3882	Suspended
0.6875	Remote Similarity	NPD3051	Approved
0.6871	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7312	Approved
0.6868	Remote Similarity	NPD4578	Approved
0.6868	Remote Similarity	NPD7311	Approved
0.6868	Remote Similarity	NPD7310	Approved
0.6868	Remote Similarity	NPD7313	Approved
0.6868	Remote Similarity	NPD4577	Approved
0.6863	Remote Similarity	NPD422	Phase 1
0.686	Remote Similarity	NPD2801	Approved
0.6859	Remote Similarity	NPD6584	Phase 3
0.6855	Remote Similarity	NPD6233	Phase 2
0.6852	Remote Similarity	NPD3748	Approved
0.6837	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7874	Approved
0.6836	Remote Similarity	NPD2970	Approved
0.6836	Remote Similarity	NPD2969	Approved
0.6832	Remote Similarity	NPD6653	Approved
0.6832	Remote Similarity	NPD6353	Approved
0.6831	Remote Similarity	NPD7309	Approved
0.6828	Remote Similarity	NPD2684	Approved
0.6826	Remote Similarity	NPD1511	Approved
0.6824	Remote Similarity	NPD7458	Discontinued
0.6821	Remote Similarity	NPD3817	Phase 2
0.6821	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2238	Phase 2
0.6813	Remote Similarity	NPD8453	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