NPASS Compound

Structure

CID216092 OpenBabel06191716002D 25 27 0 0 0 0 0 0 0 0999 V2000 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 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 -0.0000 -2.0000 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 -3.5491 -1.8090 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 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 -0.8660 -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 0.8660 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 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 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 24 1 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 16 20 1 0 0 0 0 17 19 2 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.15
Volume:	360.172
LogP:	5.392
LogD:	4.512
LogS:	-5.354
# Rotatable Bonds:	6
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	2.945
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.728
MDCK Permeability:	1.7926095097209327e-05
Pgp-inhibitor:	0.135
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.119

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	90.69125366210938%
Volume Distribution (VD):	0.784
Pgp-substrate:	8.987775802612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.201
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.735
CYP2D6-inhibitor:	0.733
CYP2D6-substrate:	0.598
CYP3A4-inhibitor:	0.669
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	11.989
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.882
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.496
Skin Sensitization:	0.337
Carcinogencity:	0.318
Eye Corrosion:	0.003
Eye Irritation:	0.073
Respiratory Toxicity:	0.796

Download Data

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

Natural Product: NPC216092

Natural Product ID:	NPC216092
*Common Name:**	9-[(2E)-3,7-Dimethylocta-2,6-Dienoxy]Furo[3,2-G]Chromen-7-One
IUPAC Name:	9-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
Synonyms:	8-Geranyloxy Psoralen
Standard InCHIKey:	SOVNCTNQAWWYAQ-OQLLNIDSSA-N
Standard InCHI:	InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-19-17(10-12-23-19)13-16-7-8-18(22)25-20(16)21/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
SMILES:	C/C(=CCOc1c2occc2cc2c1oc(=O)cc2)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1412710
PubChem CID:	5317564
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16249088]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19327990]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20973550]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Stems	n.a.	n.a.	PMID[22372931]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24798144]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24813739]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26316467]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26523463]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	Shoot Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163.1	Daucus carota var. sativa	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12746	Pleurospermum rivulorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6565	Cymbopogon goeringii	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO12746	Pleurospermum rivulorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6565	Cymbopogon goeringii	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163.1	Daucus carota var. sativa	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29169	Origanum vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO662	Angelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Ki	2
Potency	26

Activity Type	# Activity
Cell Line	1
Individual Protein	24
NON-MOLECULAR	2
Others	3
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[529303]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	19952.6	nM	PMID[529303]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	15848.9	nM	PMID[529303]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	12589.3	nM	PMID[529303]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	1258.9	nM	PMID[529303]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[529304]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[529304]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[529303]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[529304]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[529304]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29855.4	nM	PMID[529303]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[529304]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	33498.3	nM	PMID[529303]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[529304]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[529304]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	63095.7	nM	PMID[529304]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[529303]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	8912.5	nM	PMID[529303]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	7943.3	nM	PMID[529303]
NPT2	Others	Unspecified		Potency	=	1584.9	nM	PMID[529303]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[529304]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	4466.8	nM	PMID[529303]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[529304]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	20400.0	nM	PMID[529305]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	61600.0	nM	PMID[529305]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	61900.0	nM	PMID[529305]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[529304]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[529304]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1900.0	nM	PMID[529306]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[529306]

☑ 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 NPC216092 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	456
0.1-0.2	1970
0.2-0.3	4964
0.3-0.4	11314
0.4-0.5	6679
0.5-0.6	4245
0.6-0.7	6058
0.7-0.8	5288
0.8-0.85	1419
0.85-0.9	260
0.9-0.95	33
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC243509
0.9868	High Similarity	NPC33320
0.9744	High Similarity	NPC155264
0.9744	High Similarity	NPC193881
0.9744	High Similarity	NPC67450
0.9744	High Similarity	NPC210460
0.9679	High Similarity	NPC173149
0.9679	High Similarity	NPC179015
0.9615	High Similarity	NPC179464
0.956	High Similarity	NPC51404
0.9551	High Similarity	NPC78612
0.9551	High Similarity	NPC234536
0.9437	High Similarity	NPC144288
0.9346	High Similarity	NPC98028
0.9325	High Similarity	NPC107244
0.9264	High Similarity	NPC224165
0.9264	High Similarity	NPC53917
0.9245	High Similarity	NPC15819
0.9241	High Similarity	NPC264293
0.9202	High Similarity	NPC233956
0.9156	High Similarity	NPC191104
0.9103	High Similarity	NPC131725
0.9091	High Similarity	NPC88445
0.908	High Similarity	NPC281835
0.9026	High Similarity	NPC266743
0.9006	High Similarity	NPC65846
0.8994	High Similarity	NPC250076
0.8974	High Similarity	NPC474388
0.8974	High Similarity	NPC472535
0.8974	High Similarity	NPC474170
0.897	High Similarity	NPC72455
0.897	High Similarity	NPC62640
0.8961	High Similarity	NPC304443
0.8961	High Similarity	NPC74539
0.8961	High Similarity	NPC117463
0.8947	High Similarity	NPC51146
0.8947	High Similarity	NPC166858
0.8924	High Similarity	NPC250769
0.8924	High Similarity	NPC295608
0.8924	High Similarity	NPC471746
0.8924	High Similarity	NPC278010
0.891	High Similarity	NPC177839
0.8882	High Similarity	NPC14822
0.8882	High Similarity	NPC27220
0.8861	High Similarity	NPC186507
0.8839	High Similarity	NPC299923
0.8831	High Similarity	NPC246903
0.8831	High Similarity	NPC471590
0.8827	High Similarity	NPC302741
0.882	High Similarity	NPC49009
0.882	High Similarity	NPC95472
0.882	High Similarity	NPC239270
0.882	High Similarity	NPC169
0.882	High Similarity	NPC303210
0.8812	High Similarity	NPC269495
0.8805	High Similarity	NPC34725
0.8805	High Similarity	NPC284353
0.8805	High Similarity	NPC122623
0.8805	High Similarity	NPC241774
0.8805	High Similarity	NPC276059
0.8797	High Similarity	NPC68882
0.879	High Similarity	NPC5840
0.879	High Similarity	NPC189270
0.8788	High Similarity	NPC41853
0.878	High Similarity	NPC472895
0.8774	High Similarity	NPC310259
0.8773	High Similarity	NPC132054
0.8758	High Similarity	NPC113055
0.8758	High Similarity	NPC254010
0.875	High Similarity	NPC19860
0.875	High Similarity	NPC262635
0.875	High Similarity	NPC474983
0.875	High Similarity	NPC257277
0.8742	High Similarity	NPC279930
0.8742	High Similarity	NPC475895
0.8742	High Similarity	NPC41719
0.8727	High Similarity	NPC167479
0.8726	High Similarity	NPC474648
0.8712	High Similarity	NPC272722
0.871	High Similarity	NPC208584
0.8704	High Similarity	NPC477164
0.8701	High Similarity	NPC313036
0.8701	High Similarity	NPC476054
0.8696	High Similarity	NPC19097
0.8696	High Similarity	NPC310206
0.8683	High Similarity	NPC475964
0.8679	High Similarity	NPC130015
0.8679	High Similarity	NPC40033
0.8679	High Similarity	NPC38361
0.8667	High Similarity	NPC323137
0.8667	High Similarity	NPC298071
0.8662	High Similarity	NPC476342
0.8662	High Similarity	NPC183236
0.8654	High Similarity	NPC190572
0.865	High Similarity	NPC34376
0.8645	High Similarity	NPC293201
0.8645	High Similarity	NPC113089
0.8642	High Similarity	NPC15764
0.8636	High Similarity	NPC185607
0.8634	High Similarity	NPC155063
0.8625	High Similarity	NPC473664
0.8625	High Similarity	NPC189130
0.8623	High Similarity	NPC131866
0.8623	High Similarity	NPC190351
0.8618	High Similarity	NPC253616
0.8616	High Similarity	NPC473732
0.8614	High Similarity	NPC241820
0.8613	High Similarity	NPC73703
0.8608	High Similarity	NPC69752
0.8606	High Similarity	NPC187923
0.8606	High Similarity	NPC279768
0.8606	High Similarity	NPC36320
0.8599	High Similarity	NPC470511
0.8598	High Similarity	NPC475144
0.8598	High Similarity	NPC193998
0.859	High Similarity	NPC136278
0.8589	High Similarity	NPC139876
0.8581	High Similarity	NPC9966
0.8581	High Similarity	NPC70853
0.858	High Similarity	NPC270044
0.8571	High Similarity	NPC157522
0.8571	High Similarity	NPC470856
0.8571	High Similarity	NPC233776
0.8562	High Similarity	NPC304954
0.8562	High Similarity	NPC60211
0.8562	High Similarity	NPC36414
0.8562	High Similarity	NPC475116
0.8553	High Similarity	NPC148423
0.8553	High Similarity	NPC135303
0.8553	High Similarity	NPC259058
0.8553	High Similarity	NPC155882
0.8553	High Similarity	NPC201547
0.8553	High Similarity	NPC268081
0.8545	High Similarity	NPC472582
0.8544	High Similarity	NPC261548
0.8538	High Similarity	NPC104682
0.8537	High Similarity	NPC94155
0.8537	High Similarity	NPC309335
0.8537	High Similarity	NPC296540
0.8528	High Similarity	NPC238405
0.8528	High Similarity	NPC257914
0.8528	High Similarity	NPC104459
0.8526	High Similarity	NPC17262
0.8521	High Similarity	NPC65885
0.8519	High Similarity	NPC248299
0.8516	High Similarity	NPC28326
0.8516	High Similarity	NPC29536
0.8509	High Similarity	NPC128961
0.8509	High Similarity	NPC472408
0.8506	High Similarity	NPC472515
0.8506	High Similarity	NPC136095
0.8503	High Similarity	NPC186392
0.8503	High Similarity	NPC247973
0.85	High Similarity	NPC198615
0.85	High Similarity	NPC236769
0.85	High Similarity	NPC474663
0.8497	Intermediate Similarity	NPC44573
0.8494	Intermediate Similarity	NPC38914
0.8494	Intermediate Similarity	NPC204088
0.8494	Intermediate Similarity	NPC329215
0.8494	Intermediate Similarity	NPC45449
0.8494	Intermediate Similarity	NPC475369
0.8494	Intermediate Similarity	NPC259007
0.8494	Intermediate Similarity	NPC280893
0.8491	Intermediate Similarity	NPC181250
0.8485	Intermediate Similarity	NPC19948
0.8485	Intermediate Similarity	NPC471745
0.8485	Intermediate Similarity	NPC273021
0.8485	Intermediate Similarity	NPC18284
0.8481	Intermediate Similarity	NPC198427
0.8481	Intermediate Similarity	NPC205522
0.8476	Intermediate Similarity	NPC269906
0.8476	Intermediate Similarity	NPC328102
0.8476	Intermediate Similarity	NPC298093
0.8471	Intermediate Similarity	NPC296575
0.8471	Intermediate Similarity	NPC171656
0.8471	Intermediate Similarity	NPC66804
0.8466	Intermediate Similarity	NPC108456
0.8466	Intermediate Similarity	NPC78071
0.8457	Intermediate Similarity	NPC3273
0.8457	Intermediate Similarity	NPC133392
0.8457	Intermediate Similarity	NPC234255
0.8457	Intermediate Similarity	NPC478238
0.8447	Intermediate Similarity	NPC144162
0.8447	Intermediate Similarity	NPC166201
0.8447	Intermediate Similarity	NPC199773
0.8443	Intermediate Similarity	NPC475214
0.8438	Intermediate Similarity	NPC166753
0.8438	Intermediate Similarity	NPC472406
0.8438	Intermediate Similarity	NPC50728
0.8438	Intermediate Similarity	NPC29056
0.8434	Intermediate Similarity	NPC1706
0.8434	Intermediate Similarity	NPC1755
0.8434	Intermediate Similarity	NPC39305
0.8434	Intermediate Similarity	NPC263092
0.8434	Intermediate Similarity	NPC59295
0.8428	Intermediate Similarity	NPC10304
0.8428	Intermediate Similarity	NPC306788
0.8428	Intermediate Similarity	NPC63256
0.8424	Intermediate Similarity	NPC112418

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 NPC216092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	1016
0.2-0.3	1910
0.3-0.4	2701
0.4-0.5	1792
0.5-0.6	889
0.6-0.7	307
0.7-0.8	107
0.8-0.85	21
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9868	High Similarity	NPD919	Approved
0.9241	High Similarity	NPD1247	Approved
0.8961	High Similarity	NPD920	Approved
0.8947	High Similarity	NPD643	Clinical (unspecified phase)
0.8831	High Similarity	NPD642	Clinical (unspecified phase)
0.8805	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD1243	Approved
0.8634	High Similarity	NPD3882	Suspended
0.8545	High Similarity	NPD3926	Phase 2
0.8526	High Similarity	NPD6799	Approved
0.8509	High Similarity	NPD7096	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD5494	Approved
0.8447	Intermediate Similarity	NPD6801	Discontinued
0.8354	Intermediate Similarity	NPD7075	Discontinued
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8194	Intermediate Similarity	NPD2796	Approved
0.8171	Intermediate Similarity	NPD7819	Suspended
0.8171	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD1934	Approved
0.8092	Intermediate Similarity	NPD6559	Discontinued
0.807	Intermediate Similarity	NPD3818	Discontinued
0.8061	Intermediate Similarity	NPD2801	Approved
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.7963	Intermediate Similarity	NPD1512	Approved
0.7953	Intermediate Similarity	NPD6166	Phase 2
0.7953	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6232	Discontinued
0.7939	Intermediate Similarity	NPD7411	Suspended
0.7914	Intermediate Similarity	NPD5403	Approved
0.7907	Intermediate Similarity	NPD7473	Discontinued
0.7904	Intermediate Similarity	NPD5402	Approved
0.7901	Intermediate Similarity	NPD5401	Approved
0.7841	Intermediate Similarity	NPD7808	Phase 3
0.784	Intermediate Similarity	NPD1511	Approved
0.7829	Intermediate Similarity	NPD6797	Phase 2
0.7811	Intermediate Similarity	NPD3749	Approved
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD4380	Phase 2
0.7751	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7054	Approved
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD2534	Approved
0.7683	Intermediate Similarity	NPD2532	Approved
0.7683	Intermediate Similarity	NPD2533	Approved
0.7673	Intermediate Similarity	NPD1510	Phase 2
0.7673	Intermediate Similarity	NPD3748	Approved
0.767	Intermediate Similarity	NPD7472	Approved
0.767	Intermediate Similarity	NPD7074	Phase 3
0.7647	Intermediate Similarity	NPD7768	Phase 2
0.7644	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1549	Phase 2
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7613	Intermediate Similarity	NPD6832	Phase 2
0.7602	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1933	Approved
0.7595	Intermediate Similarity	NPD447	Suspended
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1240	Approved
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7528	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD1471	Phase 3
0.7469	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7439	Intermediate Similarity	NPD3750	Approved
0.7438	Intermediate Similarity	NPD1607	Approved
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5242	Approved
0.7378	Intermediate Similarity	NPD2800	Approved
0.7371	Intermediate Similarity	NPD6959	Discontinued
0.7362	Intermediate Similarity	NPD2344	Approved
0.736	Intermediate Similarity	NPD2163	Approved
0.7345	Intermediate Similarity	NPD2403	Approved
0.7345	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7294	Intermediate Similarity	NPD3226	Approved
0.7289	Intermediate Similarity	NPD3887	Approved
0.7283	Intermediate Similarity	NPD5353	Approved
0.7267	Intermediate Similarity	NPD230	Phase 1
0.7262	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3146	Approved
0.7249	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6808	Phase 2
0.7225	Intermediate Similarity	NPD4107	Approved
0.7222	Intermediate Similarity	NPD7286	Phase 2
0.7209	Intermediate Similarity	NPD6386	Approved
0.7209	Intermediate Similarity	NPD6385	Approved
0.7205	Intermediate Similarity	NPD943	Approved
0.7204	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1296	Phase 2
0.7188	Intermediate Similarity	NPD4482	Phase 3
0.7186	Intermediate Similarity	NPD2309	Approved
0.7169	Intermediate Similarity	NPD2654	Approved
0.7168	Intermediate Similarity	NPD37	Approved
0.716	Intermediate Similarity	NPD6355	Discontinued
0.7158	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2353	Approved
0.7152	Intermediate Similarity	NPD1019	Discontinued
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7135	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7128	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD9717	Approved
0.7099	Intermediate Similarity	NPD4307	Phase 2
0.7089	Intermediate Similarity	NPD3266	Approved
0.7089	Intermediate Similarity	NPD3267	Approved
0.7089	Intermediate Similarity	NPD1203	Approved
0.7081	Intermediate Similarity	NPD6798	Discontinued
0.7072	Intermediate Similarity	NPD3751	Discontinued
0.7069	Intermediate Similarity	NPD6280	Approved
0.7069	Intermediate Similarity	NPD6279	Approved
0.7062	Intermediate Similarity	NPD6234	Discontinued
0.7051	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3787	Discontinued
0.7035	Intermediate Similarity	NPD1653	Approved
0.7032	Intermediate Similarity	NPD17	Approved
0.703	Intermediate Similarity	NPD7033	Discontinued
0.7024	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5049	Phase 3
0.7012	Intermediate Similarity	NPD6651	Approved
0.7011	Intermediate Similarity	NPD5889	Approved
0.7011	Intermediate Similarity	NPD5890	Approved
0.7	Intermediate Similarity	NPD9494	Approved
0.6994	Remote Similarity	NPD4060	Phase 1
0.6982	Remote Similarity	NPD6190	Approved
0.6982	Remote Similarity	NPD2354	Approved
0.6975	Remote Similarity	NPD411	Approved
0.6975	Remote Similarity	NPD3268	Approved
0.6959	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5124	Phase 1
0.6949	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5536	Phase 2
0.6943	Remote Similarity	NPD422	Phase 1
0.6937	Remote Similarity	NPD2798	Approved
0.6931	Remote Similarity	NPD4287	Approved
0.6928	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6765	Approved
0.6919	Remote Similarity	NPD6764	Approved
0.6902	Remote Similarity	NPD1729	Discontinued
0.6899	Remote Similarity	NPD1608	Approved
0.6897	Remote Similarity	NPD7458	Discontinued
0.6897	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8127	Discontinued
0.6886	Remote Similarity	NPD2438	Suspended
0.6875	Remote Similarity	NPD2797	Approved
0.6857	Remote Similarity	NPD6585	Discontinued
0.6852	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6233	Phase 2
0.6826	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4110	Phase 3
0.6824	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6273	Approved
0.6818	Remote Similarity	NPD6873	Phase 2
0.681	Remote Similarity	NPD3027	Phase 3
0.6802	Remote Similarity	NPD5006	Approved
0.6802	Remote Similarity	NPD3057	Approved
0.6802	Remote Similarity	NPD5005	Approved
0.6798	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4288	Approved
0.6797	Remote Similarity	NPD1241	Discontinued
0.6793	Remote Similarity	NPD7228	Approved
0.6792	Remote Similarity	NPD3972	Approved
0.679	Remote Similarity	NPD3018	Phase 2
0.6788	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2979	Phase 3
0.6788	Remote Similarity	NPD1613	Approved
0.678	Remote Similarity	NPD5980	Discovery
0.6776	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6784	Approved
0.6772	Remote Similarity	NPD6785	Approved

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