NPASS Compound

Structure

CID190931 OpenBabel06191715572D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.1623 -4.0132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3497 0.0723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 1.0151 -2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4942 -0.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 -3.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4914 -0.4644 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 -2.1565 -2.6863 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 -0.9309 -1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2256 -2.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6623 -3.1472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0225 -2.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1716 -1.1974 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1623 -4.0132 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8488 -2.7496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1271 -0.9027 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 1.5000 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 1 22 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 15 22 1 6 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 25 1 0 0 0 0 19 21 2 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	371.17
Volume:	382.595
LogP:	1.263
LogD:	1.633
LogS:	-2.016
# Rotatable Bonds:	5
TPSA:	66.02
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.872
Synthetic Accessibility Score:	2.935
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.762
MDCK Permeability:	1.7560712876729667e-05
Pgp-inhibitor:	0.337
Pgp-substrate:	0.173
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	60.84138488769531%
Volume Distribution (VD):	1.765
Pgp-substrate:	28.15917205810547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.164
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.26
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.731
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.151
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	3.357
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.296
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.35
AMES Toxicity:	0.227
Rat Oral Acute Toxicity:	0.659
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.125
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC190931

Natural Product ID:	NPC190931
*Common Name:**	(-)-Demecolcine
IUPAC Name:	(7S)-1,2,3,10-tetramethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one
Synonyms:
Standard InCHIKey:	NNJPGOLRFBJNIW-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3/p+1/t15-/m0/s1
SMILES:	C[NH2+][C@H]1CCc2cc(c(c(c2-c2ccc(c(=O)cc12)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL312862
PubChem CID:	220401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004150] Hydrocarbon derivatives [CHEMONTID:0001650] Tropones

*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
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO24146	Colchicum brachyphyllum	Species	Colchicaceae	Eukaryota	n.a.	Jordanian	n.a.	PMID[15730238]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO2467	Colchicum autumnale	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31185	Phragmites communis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12126	Coix lacryma-jobi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12126.1	Coix lacryma- jobi var. ma - yuen	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21091	Rhizoma imperatae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12126	Coix lacryma-jobi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO127	Phragmites australis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2467	Colchicum autumnale	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12126	Coix lacryma-jobi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31185	Phragmites communis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO127	Phragmites australis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5913	Cneorum tricoccon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13973	Centaurea behen	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24146	Colchicum brachyphyllum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19531	Chamaecytisus prolifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO127	Phragmites australis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12126	Coix lacryma-jobi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2467	Colchicum autumnale	Species	Colchicaceae	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
AC50	12
EC50	11
ED50	1
IC50	9
MIC	4
Others	23
Potency	37

Activity Type	# Activity
Cell Line	15
Individual Protein	23
NON-MOLECULAR	3
Organism	9
Others	46
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	Log CR	=	1.2	n.a.	PMID[489256]
NPT168	Cell Line	P388	Mus musculus	Potency	=	10.8	uM kg-1	PMID[489258]
NPT3597	Individual Protein	Tubulin beta chain	Bos taurus	IC50	=	2400.0	nM	PMID[489259]
NPT168	Cell Line	P388	Mus musculus	Log 1/C	=	4.66	n.a.	PMID[489260]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	75.27	%	PMID[489263]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	40.73	%	PMID[489263]
NPT91	Cell Line	KB	Homo sapiens	ED50	<	0.25	ug ml-1	PMID[489264]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	600.0	nM	PMID[489265]
NPT397	Cell Line	NCI-H460	Homo sapiens	EC50	=	690.0	nM	PMID[489265]
NPT395	Cell Line	SF-268	Homo sapiens	EC50	=	6200.0	nM	PMID[489265]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	16.0	nM	PMID[489267]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	31.0	nM	PMID[489267]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	7.8	nM	PMID[489267]
NPT323	Cell Line	SW-620	Homo sapiens	Activity	=	31.0	nM	PMID[489267]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	25.0	nM	PMID[489267]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	103.2	nM	PMID[489268]
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	177.7	nM	PMID[489269]
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	80.9	nM	PMID[489269]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	75.0	nM	PMID[489269]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	32.6	nM	PMID[489268]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	118.9	nM	PMID[489269]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	112.2	nM	PMID[489268]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	167.9	nM	PMID[489271]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	130.0	nM	PMID[489268]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20.6	nM	PMID[489268]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	237.1	nM	PMID[489271]
NPT585	Individual Protein	Nuclear receptor subfamily 0 group B member 1	Homo sapiens	IC50	>	834.47	nM	PMID[489270]
NPT1283	Individual Protein	Paired box protein Pax-8	Homo sapiens	AC50	<	260.0	nM	PMID[489270]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	64.7	%	PMID[489274]
NPT543	Individual Protein	Pregnane X receptor	Homo sapiens	Efficacy	=	51.1	%	PMID[489276]
NPT158	Individual Protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Efficacy	=	103.0	%	PMID[489276]
NPT543	Individual Protein	Pregnane X receptor	Homo sapiens	EC50	=	12600.0	nM	PMID[489276]
NPT158	Individual Protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	EC50	=	90.0	nM	PMID[489276]
NPT543	Individual Protein	Pregnane X receptor	Homo sapiens	EC50	=	14100.0	nM	PMID[489276]
NPT543	Individual Protein	Pregnane X receptor	Homo sapiens	Efficacy	=	103.0	%	PMID[489276]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	60.1	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	375.8	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	106.8	nM	PubChem BioAssay data set
NPT35	Others	n.a.		LogD	=	1.37	n.a.	PMID[489256]
NPT35	Others	n.a.		LogP	=	1.53	n.a.	PMID[489257]
NPT32	Organism	Mus musculus	Mus musculus	Log 1/LD50	=	3.63	n.a.	PMID[489257]
NPT518	Protein Complex	Tubulin	Homo sapiens	Tubulin binding	=	93.0	%	PMID[489258]
NPT32	Organism	Mus musculus	Mus musculus	Toxicity	=	21.6	uM kg-1	PMID[489258]
NPT32	Organism	Mus musculus	Mus musculus	Toxicity	=	236.7	uM kg-1	PMID[489258]
NPT32	Organism	Mus musculus	Mus musculus	Toxicity	=	237.0	mg kg-1	PMID[489259]
NPT35	Others	n.a.		LogP	=	1.53	n.a.	PMID[489260]
NPT35	Others	n.a.		LogP	=	1.37	n.a.	PMID[489261]
NPT2	Others	Unspecified		IC50	=	2400.0	nM	PMID[489262]
NPT140	Organism	Artemia	Artemia	LC50	=	61.0	ug.mL-1	PMID[489265]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	500.0	ug.mL-1	PMID[489265]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	500.0	ug.mL-1	PMID[489265]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	500.0	ug.mL-1	PMID[489265]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	500.0	ug.mL-1	PMID[489265]
NPT2	Others	Unspecified		IC50	=	3580.0	nM	PMID[489267]
NPT2	Others	Unspecified		EC50	=	85.0	nM	PMID[489268]
NPT2	Others	Unspecified		EC50	<	100.0	nM	PMID[489268]
NPT2	Others	Unspecified		EC50	=	78.0	nM	PMID[489268]
NPT2	Others	Unspecified		EC50	=	80.0	nM	PMID[489268]
NPT2	Others	Unspecified		IC50	<	160.0	nM	PMID[489268]
NPT2	Others	Unspecified		IC50	>	80000.0	nM	PMID[489268]
NPT35	Others	n.a.		IC50	>	67595.0	nM	PMID[489270]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	11875.4	nM	PMID[489272]
NPT2	Others	Unspecified		Potency	n.a.	631.0	nM	PMID[489268]
NPT2	Others	Unspecified		AC50	=	6350.0	nM	PMID[489273]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	10583.9	nM	PMID[489272]
NPT2	Others	Unspecified		AC50	=	113.0	nM	PMID[489273]
NPT2	Others	Unspecified		AC50	=	61.5	nM	PMID[489273]
NPT2	Others	Unspecified		AC50	=	48.8	nM	PMID[489273]
NPT2	Others	Unspecified		AC50	=	217.0	nM	PMID[489273]
NPT2	Others	Unspecified		AC50	=	96.7	nM	PMID[489273]
NPT2	Others	Unspecified		AC50	=	96.6	nM	PMID[489273]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	14950.2	nM	PMID[489272]
NPT2	Others	Unspecified		AC50	=	234.0	nM	PMID[489273]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[489271]
NPT2	Others	Unspecified		AC50	=	318.0	nM	PMID[489273]
NPT2	Others	Unspecified		AC50	>	100000.0	nM	PMID[489273]
NPT2	Others	Unspecified		Potency	n.a.	668.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	42.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	213.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	118.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	334.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4730.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	84.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	149.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	53.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	26.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	47.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	237.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	33.5	nM	PubChem BioAssay data set

☑ 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 NPC190931 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	314
0.1-0.2	1783
0.2-0.3	7421
0.3-0.4	10479
0.4-0.5	4860
0.5-0.6	9682
0.6-0.7	7664
0.7-0.8	480
0.8-0.85	2
0.85-0.9	3
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC218575
0.9542	High Similarity	NPC188120
0.9542	High Similarity	NPC53146
0.9542	High Similarity	NPC286790
0.9079	High Similarity	NPC108957
0.9079	High Similarity	NPC226941
0.9079	High Similarity	NPC44642
0.9079	High Similarity	NPC14005
0.879	High Similarity	NPC202839
0.879	High Similarity	NPC66678
0.8679	High Similarity	NPC189782
0.8344	Intermediate Similarity	NPC3906
0.8231	Intermediate Similarity	NPC262641
0.8095	Intermediate Similarity	NPC291847
0.8063	Intermediate Similarity	NPC114124
0.7964	Intermediate Similarity	NPC204947
0.7891	Intermediate Similarity	NPC105513
0.7888	Intermediate Similarity	NPC8337
0.7888	Intermediate Similarity	NPC85747
0.7799	Intermediate Similarity	NPC473934
0.7778	Intermediate Similarity	NPC476579
0.7742	Intermediate Similarity	NPC253429
0.7738	Intermediate Similarity	NPC39103
0.7738	Intermediate Similarity	NPC2770
0.7635	Intermediate Similarity	NPC298486
0.7633	Intermediate Similarity	NPC3375
0.7633	Intermediate Similarity	NPC255607
0.7605	Intermediate Similarity	NPC329837
0.7605	Intermediate Similarity	NPC7393
0.76	Intermediate Similarity	NPC258695
0.76	Intermediate Similarity	NPC243454
0.76	Intermediate Similarity	NPC470879
0.76	Intermediate Similarity	NPC475479
0.76	Intermediate Similarity	NPC474507
0.756	Intermediate Similarity	NPC226428
0.7557	Intermediate Similarity	NPC32413
0.7557	Intermediate Similarity	NPC239584
0.7557	Intermediate Similarity	NPC474506
0.7543	Intermediate Similarity	NPC23219
0.7529	Intermediate Similarity	NPC24465
0.7529	Intermediate Similarity	NPC180306
0.7516	Intermediate Similarity	NPC113236
0.7516	Intermediate Similarity	NPC214036
0.7515	Intermediate Similarity	NPC476580
0.75	Intermediate Similarity	NPC83198
0.75	Intermediate Similarity	NPC204908
0.7486	Intermediate Similarity	NPC173416
0.7486	Intermediate Similarity	NPC476577
0.7486	Intermediate Similarity	NPC112575
0.7486	Intermediate Similarity	NPC148709
0.7485	Intermediate Similarity	NPC13916
0.7485	Intermediate Similarity	NPC264850
0.7484	Intermediate Similarity	NPC160692
0.747	Intermediate Similarity	NPC475557
0.745	Intermediate Similarity	NPC211992
0.7439	Intermediate Similarity	NPC60538
0.7439	Intermediate Similarity	NPC207824
0.7414	Intermediate Similarity	NPC472894
0.7396	Intermediate Similarity	NPC118804
0.7396	Intermediate Similarity	NPC106786
0.7389	Intermediate Similarity	NPC57036
0.7384	Intermediate Similarity	NPC56887
0.7384	Intermediate Similarity	NPC193853
0.7384	Intermediate Similarity	NPC223077
0.7381	Intermediate Similarity	NPC57512
0.7381	Intermediate Similarity	NPC170503
0.7381	Intermediate Similarity	NPC126519
0.7381	Intermediate Similarity	NPC203784
0.7378	Intermediate Similarity	NPC59907
0.7378	Intermediate Similarity	NPC37144
0.7375	Intermediate Similarity	NPC328750
0.7375	Intermediate Similarity	NPC144284
0.7375	Intermediate Similarity	NPC188163
0.7375	Intermediate Similarity	NPC474915
0.7375	Intermediate Similarity	NPC213206
0.7371	Intermediate Similarity	NPC190783
0.7371	Intermediate Similarity	NPC4669
0.7371	Intermediate Similarity	NPC232386
0.7371	Intermediate Similarity	NPC152680
0.7368	Intermediate Similarity	NPC124433
0.7368	Intermediate Similarity	NPC476569
0.7368	Intermediate Similarity	NPC59567
0.7368	Intermediate Similarity	NPC64391
0.7368	Intermediate Similarity	NPC293871
0.7365	Intermediate Similarity	NPC2295
0.7365	Intermediate Similarity	NPC477564
0.7356	Intermediate Similarity	NPC26240
0.7356	Intermediate Similarity	NPC75958
0.7356	Intermediate Similarity	NPC69712
0.7356	Intermediate Similarity	NPC6152
0.7356	Intermediate Similarity	NPC477562
0.7349	Intermediate Similarity	NPC76213
0.7349	Intermediate Similarity	NPC277669
0.7348	Intermediate Similarity	NPC186546
0.7348	Intermediate Similarity	NPC476576
0.7346	Intermediate Similarity	NPC294249
0.733	Intermediate Similarity	NPC329969
0.7326	Intermediate Similarity	NPC209377
0.7321	Intermediate Similarity	NPC99659
0.7321	Intermediate Similarity	NPC325871
0.7321	Intermediate Similarity	NPC187022
0.7321	Intermediate Similarity	NPC80129
0.7317	Intermediate Similarity	NPC106295
0.7317	Intermediate Similarity	NPC474446
0.7317	Intermediate Similarity	NPC476144
0.7317	Intermediate Similarity	NPC51957
0.7317	Intermediate Similarity	NPC210437
0.7317	Intermediate Similarity	NPC16107
0.7314	Intermediate Similarity	NPC19520
0.7314	Intermediate Similarity	NPC239775
0.7314	Intermediate Similarity	NPC115284
0.7314	Intermediate Similarity	NPC276890
0.7314	Intermediate Similarity	NPC63646
0.7314	Intermediate Similarity	NPC10908
0.7314	Intermediate Similarity	NPC149090
0.7314	Intermediate Similarity	NPC76682
0.7314	Intermediate Similarity	NPC227060
0.7314	Intermediate Similarity	NPC317439
0.7314	Intermediate Similarity	NPC198498
0.7314	Intermediate Similarity	NPC317145
0.7312	Intermediate Similarity	NPC314682
0.7308	Intermediate Similarity	NPC175890
0.7308	Intermediate Similarity	NPC274661
0.7308	Intermediate Similarity	NPC11296
0.7308	Intermediate Similarity	NPC48490
0.7308	Intermediate Similarity	NPC82457
0.7308	Intermediate Similarity	NPC281581
0.7284	Intermediate Similarity	NPC136860
0.7284	Intermediate Similarity	NPC128019
0.7284	Intermediate Similarity	NPC476567
0.7273	Intermediate Similarity	NPC477020
0.7273	Intermediate Similarity	NPC7467
0.7273	Intermediate Similarity	NPC66341
0.7273	Intermediate Similarity	NPC129518
0.7273	Intermediate Similarity	NPC12424
0.7273	Intermediate Similarity	NPC192135
0.7273	Intermediate Similarity	NPC251580
0.7273	Intermediate Similarity	NPC41376
0.7273	Intermediate Similarity	NPC471986
0.7268	Intermediate Similarity	NPC63152
0.7268	Intermediate Similarity	NPC191132
0.7268	Intermediate Similarity	NPC60295
0.7267	Intermediate Similarity	NPC323204
0.7253	Intermediate Similarity	NPC208890
0.7241	Intermediate Similarity	NPC284842
0.7235	Intermediate Similarity	NPC476572
0.723	Intermediate Similarity	NPC120075
0.7226	Intermediate Similarity	NPC181675
0.7226	Intermediate Similarity	NPC283114
0.7226	Intermediate Similarity	NPC207702
0.7226	Intermediate Similarity	NPC149008
0.7219	Intermediate Similarity	NPC123323
0.7219	Intermediate Similarity	NPC169742
0.7215	Intermediate Similarity	NPC32778
0.7205	Intermediate Similarity	NPC470962
0.72	Intermediate Similarity	NPC222175
0.7191	Intermediate Similarity	NPC241704
0.7191	Intermediate Similarity	NPC293093
0.7189	Intermediate Similarity	NPC256124
0.7188	Intermediate Similarity	NPC471182
0.7179	Intermediate Similarity	NPC160193
0.7176	Intermediate Similarity	NPC160931
0.7176	Intermediate Similarity	NPC37205
0.7176	Intermediate Similarity	NPC323443
0.7176	Intermediate Similarity	NPC180756
0.7171	Intermediate Similarity	NPC264885
0.7171	Intermediate Similarity	NPC288238
0.717	Intermediate Similarity	NPC145769
0.717	Intermediate Similarity	NPC11147
0.716	Intermediate Similarity	NPC474414
0.7159	Intermediate Similarity	NPC118274
0.7159	Intermediate Similarity	NPC168753
0.7152	Intermediate Similarity	NPC232883
0.7152	Intermediate Similarity	NPC475856
0.7151	Intermediate Similarity	NPC475780
0.7151	Intermediate Similarity	NPC121400
0.7143	Intermediate Similarity	NPC18306
0.7143	Intermediate Similarity	NPC214629
0.7135	Intermediate Similarity	NPC117717
0.7135	Intermediate Similarity	NPC129603
0.7134	Intermediate Similarity	NPC19242
0.7134	Intermediate Similarity	NPC244338
0.7134	Intermediate Similarity	NPC126836
0.7133	Intermediate Similarity	NPC475961
0.7133	Intermediate Similarity	NPC308217
0.7133	Intermediate Similarity	NPC254625
0.7126	Intermediate Similarity	NPC211296
0.7124	Intermediate Similarity	NPC108545
0.7119	Intermediate Similarity	NPC10871
0.7118	Intermediate Similarity	NPC244112
0.7112	Intermediate Similarity	NPC281629
0.7111	Intermediate Similarity	NPC32154
0.7111	Intermediate Similarity	NPC244554
0.711	Intermediate Similarity	NPC153631
0.7108	Intermediate Similarity	NPC476151
0.7107	Intermediate Similarity	NPC274441
0.7105	Intermediate Similarity	NPC477886
0.7102	Intermediate Similarity	NPC470324
0.7093	Intermediate Similarity	NPC329640
0.7091	Intermediate Similarity	NPC50696

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 NPC190931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	795
0.2-0.3	1118
0.3-0.4	2209
0.4-0.5	2669
0.5-0.6	1512
0.6-0.7	585
0.7-0.8	57
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4585	Approved
0.9079	High Similarity	NPD5089	Approved
0.9079	High Similarity	NPD5090	Approved
0.7702	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1424	Approved
0.7584	Intermediate Similarity	NPD6841	Approved
0.7584	Intermediate Similarity	NPD6843	Phase 3
0.7584	Intermediate Similarity	NPD6842	Approved
0.756	Intermediate Similarity	NPD4055	Discovery
0.7516	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6111	Discontinued
0.7419	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7124	Phase 2
0.7389	Intermediate Similarity	NPD2653	Approved
0.7375	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4005	Discontinued
0.7346	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7298	Approved
0.7317	Intermediate Similarity	NPD4584	Approved
0.7314	Intermediate Similarity	NPD8251	Approved
0.7314	Intermediate Similarity	NPD8099	Discontinued
0.7314	Intermediate Similarity	NPD8252	Approved
0.7273	Intermediate Similarity	NPD8156	Discontinued
0.7256	Intermediate Similarity	NPD5297	Approved
0.7229	Intermediate Similarity	NPD3641	Approved
0.7229	Intermediate Similarity	NPD6030	Approved
0.7229	Intermediate Similarity	NPD3640	Phase 3
0.7229	Intermediate Similarity	NPD6031	Approved
0.7229	Intermediate Similarity	NPD3639	Approved
0.7222	Intermediate Similarity	NPD3060	Approved
0.7209	Intermediate Similarity	NPD5709	Phase 3
0.7193	Intermediate Similarity	NPD6788	Approved
0.7186	Intermediate Similarity	NPD3687	Approved
0.7186	Intermediate Similarity	NPD3686	Approved
0.7169	Intermediate Similarity	NPD1349	Approved
0.7169	Intermediate Similarity	NPD1350	Approved
0.7169	Intermediate Similarity	NPD1351	Approved
0.7168	Intermediate Similarity	NPD4666	Phase 3
0.7126	Intermediate Similarity	NPD6107	Approved
0.7102	Intermediate Similarity	NPD2898	Approved
0.7072	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3489	Phase 3
0.7055	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5242	Approved
0.7041	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2563	Approved
0.7035	Intermediate Similarity	NPD2560	Approved
0.7033	Intermediate Similarity	NPD8053	Approved
0.7033	Intermediate Similarity	NPD8054	Approved
0.703	Intermediate Similarity	NPD2677	Approved
0.7022	Intermediate Similarity	NPD2163	Approved
0.7012	Intermediate Similarity	NPD4162	Approved
0.7006	Intermediate Similarity	NPD3157	Approved
0.7006	Intermediate Similarity	NPD4481	Phase 3
0.7006	Intermediate Similarity	NPD3158	Phase 1
0.6989	Remote Similarity	NPD4166	Phase 2
0.6983	Remote Similarity	NPD42	Phase 2
0.6983	Remote Similarity	NPD6042	Phase 2
0.6978	Remote Similarity	NPD2968	Approved
0.6978	Remote Similarity	NPD2971	Approved
0.6977	Remote Similarity	NPD2977	Approved
0.6977	Remote Similarity	NPD2978	Approved
0.6975	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD52	Approved
0.6964	Remote Similarity	NPD7526	Approved
0.6964	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5241	Discontinued
0.6923	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5976	Discontinued
0.6914	Remote Similarity	NPD6895	Approved
0.6914	Remote Similarity	NPD6896	Approved
0.6913	Remote Similarity	NPD595	Approved
0.6913	Remote Similarity	NPD593	Approved
0.6909	Remote Similarity	NPD2654	Approved
0.6905	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6386	Approved
0.686	Remote Similarity	NPD6385	Approved
0.6845	Remote Similarity	NPD1774	Approved
0.6845	Remote Similarity	NPD4357	Discontinued
0.6842	Remote Similarity	NPD4017	Approved
0.6842	Remote Similarity	NPD2974	Approved
0.6842	Remote Similarity	NPD2973	Approved
0.6842	Remote Similarity	NPD2975	Approved
0.6839	Remote Similarity	NPD5005	Approved
0.6839	Remote Similarity	NPD5006	Approved
0.6832	Remote Similarity	NPD2238	Phase 2
0.6831	Remote Similarity	NPD7549	Discontinued
0.6826	Remote Similarity	NPD2219	Phase 1
0.6826	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3382	Approved
0.6821	Remote Similarity	NPD3383	Approved
0.6821	Remote Similarity	NPD3384	Approved
0.6813	Remote Similarity	NPD6297	Approved
0.6813	Remote Similarity	NPD5718	Phase 2
0.6807	Remote Similarity	NPD4237	Approved
0.6807	Remote Similarity	NPD4236	Phase 3
0.6805	Remote Similarity	NPD3536	Discontinued
0.6802	Remote Similarity	NPD6875	Approved
0.6802	Remote Similarity	NPD6876	Approved
0.68	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3051	Approved
0.6798	Remote Similarity	NPD6071	Discontinued
0.6784	Remote Similarity	NPD4210	Discontinued
0.6776	Remote Similarity	NPD7038	Approved
0.6776	Remote Similarity	NPD7039	Approved
0.6768	Remote Similarity	NPD2156	Approved
0.6768	Remote Similarity	NPD2154	Approved
0.6768	Remote Similarity	NPD2155	Approved
0.6765	Remote Similarity	NPD2676	Approved
0.6765	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2675	Approved
0.6763	Remote Similarity	NPD4772	Phase 2
0.6763	Remote Similarity	NPD4773	Phase 2
0.676	Remote Similarity	NPD2969	Approved
0.676	Remote Similarity	NPD2970	Approved
0.675	Remote Similarity	NPD3179	Approved
0.675	Remote Similarity	NPD3180	Approved
0.6748	Remote Similarity	NPD2568	Approved
0.6748	Remote Similarity	NPD2492	Phase 1
0.6746	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2649	Approved
0.6744	Remote Similarity	NPD2651	Approved
0.6743	Remote Similarity	NPD5977	Approved
0.6743	Remote Similarity	NPD5353	Approved
0.6743	Remote Similarity	NPD5978	Approved
0.6739	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4580	Approved
0.6736	Remote Similarity	NPD4107	Approved
0.673	Remote Similarity	NPD3018	Phase 2
0.6722	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4420	Approved
0.6707	Remote Similarity	NPD2200	Suspended
0.6705	Remote Similarity	NPD4678	Approved
0.6705	Remote Similarity	NPD4675	Approved
0.6703	Remote Similarity	NPD5095	Phase 3
0.6703	Remote Similarity	NPD5096	Phase 3
0.6701	Remote Similarity	NPD2493	Approved
0.6701	Remote Similarity	NPD3452	Approved
0.6701	Remote Similarity	NPD3450	Approved
0.6701	Remote Similarity	NPD2494	Approved
0.6687	Remote Similarity	NPD596	Approved
0.6687	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD600	Approved
0.6687	Remote Similarity	NPD1375	Discontinued
0.6685	Remote Similarity	NPD5677	Discontinued
0.6667	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1132	Approved
0.6667	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6853	Approved
0.6667	Remote Similarity	NPD6618	Phase 2
0.6667	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7110	Phase 1
0.6667	Remote Similarity	NPD6851	Approved
0.6667	Remote Similarity	NPD1136	Approved
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD602	Approved
0.6667	Remote Similarity	NPD2490	Approved
0.6667	Remote Similarity	NPD2488	Approved
0.6667	Remote Similarity	NPD2245	Discovery
0.6667	Remote Similarity	NPD1130	Approved
0.6667	Remote Similarity	NPD599	Approved
0.6667	Remote Similarity	NPD3705	Approved
0.6649	Remote Similarity	NPD7906	Approved
0.6649	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7153	Discontinued
0.6647	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3027	Phase 3
0.6632	Remote Similarity	NPD7296	Approved
0.6631	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2489	Approved
0.663	Remote Similarity	NPD27	Approved
0.6628	Remote Similarity	NPD4727	Phase 1
0.6624	Remote Similarity	NPD2981	Phase 2
0.6623	Remote Similarity	NPD5283	Phase 1
0.6615	Remote Similarity	NPD4482	Phase 3
0.6612	Remote Similarity	NPD3933	Discontinued
0.6611	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3882	Suspended
0.6608	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3146	Approved
0.6605	Remote Similarity	NPD5110	Phase 2
0.6605	Remote Similarity	NPD5109	Approved
0.6605	Remote Similarity	NPD5111	Phase 2
0.6605	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1336	Approved
0.6605	Remote Similarity	NPD598	Approved
0.6605	Remote Similarity	NPD1039	Discontinued
0.6605	Remote Similarity	NPD601	Approved
0.6605	Remote Similarity	NPD597	Approved
0.6604	Remote Similarity	NPD3053	Approved
0.6604	Remote Similarity	NPD3055	Approved
0.6599	Remote Similarity	NPD4583	Approved
0.6599	Remote Similarity	NPD4582	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