NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	1.42
LogD:	1.694
LogS:	-3.234
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	4.499
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.528
MDCK Permeability:	3.2791183912195265e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.106
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.354
Plasma Protein Binding (PPB):	47.31745529174805%
Volume Distribution (VD):	0.771
Pgp-substrate:	42.54893493652344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.238
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.71
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	6.188
Half-life (T1/2):	0.683

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.277
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.772
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.518
Carcinogencity:	0.628
Eye Corrosion:	0.863
Eye Irritation:	0.948
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC79549

Natural Product ID:	NPC79549
*Common Name:**	(3As,6R,6Ar,9R,9As,9Bs)-6,9-Dihydroxy-6,9-Dimethyl-3-Methylenedecahydroazuleno[4,5-B]Furan-2(9Bh)-One
IUPAC Name:	(3aS,6R,6aR,9R,9aS,9bS)-6,9-dihydroxy-6,9-dimethyl-3-methylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	VHFXPBHLQOPQHJ-ABBQYLIMSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-8-9-4-6-14(2,17)10-5-7-15(3,18)11(10)12(9)19-13(8)16/h9-12,17-18H,1,4-7H2,2-3H3/t9-,10+,11-,12-,14+,15+/m0/s1
SMILES:	O=C1O[C@H]2[C@H](C1=C)CC[C@@]([C@H]1[C@@H]2[C@](C)(O)CC1)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2206436
PubChem CID:	5319198
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3987/COM-96-7609.]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075784]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	stem	n.a.	PMID[10096848]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	root	n.a.	PMID[10096848]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	root and stem	n.a.	n.a.	PMID[10096848]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1431939]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038566]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[16964757]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18081254]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23059629]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	Wood	n.a.	n.a.	PMID[7119806]
NPO23020	Aristolochia fangchi	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242.1	Phellodendron chinense var. glabriusculum	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22930	Aristolochia moupinensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9279	Thalictrum dasycarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29316	Thalictrum baicalense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7780	Thalictrum foetidum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23519	Coptis teetoides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18832	Berberis thunbergii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2114.1	Thalictrum minus var. hypoleucum	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18295	Berberis amurensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11640	Berberis fortunei	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29316	Thalictrum baicalense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9279	Thalictrum dasycarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23020	Aristolochia fangchi	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7780	Thalictrum foetidum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242.1	Phellodendron chinense var. glabriusculum	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18295	Berberis amurensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22930	Aristolochia moupinensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18832	Berberis thunbergii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23519	Coptis teetoides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2114.1	Thalictrum minus var. hypoleucum	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18295	Berberis amurensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18832	Berberis thunbergii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23020	Aristolochia fangchi	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22930	Aristolochia moupinensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16163	Aristolochia heterophylla	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11640	Berberis fortunei	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14814	Aristolochia contorta	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24916	Aristolochia debilis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9279	Thalictrum dasycarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18832	Berberis thunbergii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4824	Cocculus trilobus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23519	Coptis teetoides	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12690	Caltha palustris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29316	Thalictrum baicalense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7780	Thalictrum foetidum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11640	Berberis fortunei	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18295	Berberis amurensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20412	Magnolia grandiflora	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2114.1	Thalictrum minus var. hypoleucum	Varieties	Ranunculaceae	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	2
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	21900.0	nM	PMID[520086]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	84.8	%	PMID[520086]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	84.9	%	PMID[520086]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	89.9	%	PMID[520086]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	88.5	%	PMID[520086]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17900.0	nM	PMID[520086]

☑ 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 NPC79549 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	241
0.1-0.2	1777
0.2-0.3	6579
0.3-0.4	15450
0.4-0.5	9274
0.5-0.6	6560
0.6-0.7	2298
0.7-0.8	348
0.8-0.85	73
0.85-0.9	52
0.9-0.95	37
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.988	High Similarity	NPC215556
0.9762	High Similarity	NPC216284
0.9647	High Similarity	NPC155215
0.9634	High Similarity	NPC284534
0.9634	High Similarity	NPC300082
0.9634	High Similarity	NPC204105
0.9535	High Similarity	NPC258216
0.9412	High Similarity	NPC155935
0.939	High Similarity	NPC245665
0.9318	High Similarity	NPC163228
0.9318	High Similarity	NPC472873
0.9302	High Similarity	NPC54065
0.9302	High Similarity	NPC35809
0.9302	High Similarity	NPC297474
0.9294	High Similarity	NPC178875
0.9294	High Similarity	NPC217983
0.9294	High Similarity	NPC207114
0.9286	High Similarity	NPC187661
0.9195	High Similarity	NPC29821
0.9195	High Similarity	NPC171360
0.9195	High Similarity	NPC35959
0.9195	High Similarity	NPC293001
0.9195	High Similarity	NPC184063
0.9195	High Similarity	NPC63193
0.9195	High Similarity	NPC133888
0.9195	High Similarity	NPC57304
0.9186	High Similarity	NPC472872
0.9176	High Similarity	NPC118601
0.9157	High Similarity	NPC111409
0.9101	High Similarity	NPC52044
0.9101	High Similarity	NPC476053
0.9101	High Similarity	NPC67584
0.908	High Similarity	NPC19087
0.9059	High Similarity	NPC56593
0.9048	High Similarity	NPC194859
0.9048	High Similarity	NPC224386
0.9036	High Similarity	NPC246076
0.9024	High Similarity	NPC156658
0.9024	High Similarity	NPC258965
0.9011	High Similarity	NPC45125
0.9	High Similarity	NPC213078
0.8989	High Similarity	NPC323008
0.8989	High Similarity	NPC198853
0.8989	High Similarity	NPC262133
0.8989	High Similarity	NPC470013
0.8989	High Similarity	NPC127019
0.8989	High Similarity	NPC470010
0.8977	High Similarity	NPC133698
0.8977	High Similarity	NPC131209
0.8966	High Similarity	NPC38392
0.8953	High Similarity	NPC24728
0.8953	High Similarity	NPC270270
0.8929	High Similarity	NPC128246
0.8913	High Similarity	NPC186861
0.8913	High Similarity	NPC471381
0.8901	High Similarity	NPC181151
0.8901	High Similarity	NPC161493
0.8901	High Similarity	NPC311904
0.8901	High Similarity	NPC471150
0.8889	High Similarity	NPC170120
0.8889	High Similarity	NPC213698
0.8876	High Similarity	NPC473234
0.8876	High Similarity	NPC60386
0.8876	High Similarity	NPC153590
0.8876	High Similarity	NPC308656
0.8876	High Similarity	NPC473263
0.8876	High Similarity	NPC473273
0.8864	High Similarity	NPC301969
0.8864	High Similarity	NPC37607
0.8851	High Similarity	NPC91248
0.8851	High Similarity	NPC471149
0.8837	High Similarity	NPC67493
0.8837	High Similarity	NPC309757
0.8837	High Similarity	NPC304558
0.8837	High Similarity	NPC236692
0.8804	High Similarity	NPC221615
0.8791	High Similarity	NPC142529
0.8791	High Similarity	NPC18019
0.8791	High Similarity	NPC91771
0.8791	High Similarity	NPC24956
0.8778	High Similarity	NPC477131
0.8764	High Similarity	NPC475925
0.875	High Similarity	NPC283409
0.8736	High Similarity	NPC201658
0.8696	High Similarity	NPC474313
0.869	High Similarity	NPC126248
0.8667	High Similarity	NPC472874
0.8667	High Similarity	NPC200237
0.8636	High Similarity	NPC224652
0.8621	High Similarity	NPC470242
0.8621	High Similarity	NPC64153
0.8605	High Similarity	NPC156485
0.8571	High Similarity	NPC473331
0.8556	High Similarity	NPC286341
0.8556	High Similarity	NPC191339
0.8539	High Similarity	NPC4986
0.8523	High Similarity	NPC190753
0.8506	High Similarity	NPC235792
0.8495	Intermediate Similarity	NPC108475
0.8495	Intermediate Similarity	NPC170143
0.8495	Intermediate Similarity	NPC213947
0.8462	Intermediate Similarity	NPC135776
0.8454	Intermediate Similarity	NPC54737
0.8454	Intermediate Similarity	NPC44004
0.8421	Intermediate Similarity	NPC150923
0.8421	Intermediate Similarity	NPC171759
0.8409	Intermediate Similarity	NPC162071
0.8333	Intermediate Similarity	NPC168679
0.8333	Intermediate Similarity	NPC12872
0.8316	Intermediate Similarity	NPC70865
0.8293	Intermediate Similarity	NPC143979
0.8293	Intermediate Similarity	NPC320537
0.8283	Intermediate Similarity	NPC68248
0.828	Intermediate Similarity	NPC304886
0.8261	Intermediate Similarity	NPC475788
0.8247	Intermediate Similarity	NPC124881
0.8211	Intermediate Similarity	NPC49833
0.8211	Intermediate Similarity	NPC249171
0.82	Intermediate Similarity	NPC115352
0.82	Intermediate Similarity	NPC139838
0.82	Intermediate Similarity	NPC59489
0.8182	Intermediate Similarity	NPC154893
0.8182	Intermediate Similarity	NPC16887
0.8182	Intermediate Similarity	NPC53011
0.8182	Intermediate Similarity	NPC37005
0.8144	Intermediate Similarity	NPC86077
0.814	Intermediate Similarity	NPC51507
0.8132	Intermediate Similarity	NPC32922
0.8111	Intermediate Similarity	NPC186148
0.8105	Intermediate Similarity	NPC304445
0.8105	Intermediate Similarity	NPC236580
0.8085	Intermediate Similarity	NPC167893
0.8085	Intermediate Similarity	NPC475900
0.8085	Intermediate Similarity	NPC224689
0.8081	Intermediate Similarity	NPC243998
0.8081	Intermediate Similarity	NPC223450
0.8068	Intermediate Similarity	NPC54468
0.8061	Intermediate Similarity	NPC473148
0.8046	Intermediate Similarity	NPC47635
0.8043	Intermediate Similarity	NPC474323
0.8043	Intermediate Similarity	NPC246173
0.8043	Intermediate Similarity	NPC206614
0.8022	Intermediate Similarity	NPC177629
0.8022	Intermediate Similarity	NPC58219
0.8	Intermediate Similarity	NPC208223
0.8	Intermediate Similarity	NPC238593
0.8	Intermediate Similarity	NPC26617
0.8	Intermediate Similarity	NPC476009
0.8	Intermediate Similarity	NPC126156
0.7959	Intermediate Similarity	NPC80144
0.7935	Intermediate Similarity	NPC92974
0.7931	Intermediate Similarity	NPC73052
0.7931	Intermediate Similarity	NPC276356
0.7931	Intermediate Similarity	NPC6823
0.7931	Intermediate Similarity	NPC290508
0.7931	Intermediate Similarity	NPC293418
0.7917	Intermediate Similarity	NPC261372
0.7917	Intermediate Similarity	NPC58267
0.7917	Intermediate Similarity	NPC263674
0.7917	Intermediate Similarity	NPC477949
0.79	Intermediate Similarity	NPC166115
0.7895	Intermediate Similarity	NPC469873
0.7895	Intermediate Similarity	NPC37408
0.7885	Intermediate Similarity	NPC273242
0.7879	Intermediate Similarity	NPC221421
0.7865	Intermediate Similarity	NPC128429
0.7857	Intermediate Similarity	NPC67296
0.7826	Intermediate Similarity	NPC202672
0.7816	Intermediate Similarity	NPC19841
0.7816	Intermediate Similarity	NPC182550
0.7812	Intermediate Similarity	NPC474297
0.781	Intermediate Similarity	NPC121816
0.7805	Intermediate Similarity	NPC5714
0.7802	Intermediate Similarity	NPC474762
0.7802	Intermediate Similarity	NPC476015
0.7802	Intermediate Similarity	NPC474949
0.7802	Intermediate Similarity	NPC475019
0.7789	Intermediate Similarity	NPC474338
0.7778	Intermediate Similarity	NPC138647
0.7778	Intermediate Similarity	NPC470238
0.7767	Intermediate Similarity	NPC471884
0.7766	Intermediate Similarity	NPC12172
0.7766	Intermediate Similarity	NPC184463
0.7766	Intermediate Similarity	NPC70251
0.7766	Intermediate Similarity	NPC208886
0.7766	Intermediate Similarity	NPC475881
0.7753	Intermediate Similarity	NPC89555
0.7742	Intermediate Similarity	NPC212664
0.7742	Intermediate Similarity	NPC307411
0.7736	Intermediate Similarity	NPC170692
0.7736	Intermediate Similarity	NPC255450
0.7727	Intermediate Similarity	NPC69271
0.7727	Intermediate Similarity	NPC476625
0.7727	Intermediate Similarity	NPC74673
0.7717	Intermediate Similarity	NPC5130
0.7717	Intermediate Similarity	NPC160138
0.77	Intermediate Similarity	NPC475928
0.7692	Intermediate Similarity	NPC304509
0.7692	Intermediate Similarity	NPC149725
0.7692	Intermediate Similarity	NPC165162

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 NPC79549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	2514
0.2-0.3	3930
0.3-0.4	1685
0.4-0.5	435
0.5-0.6	266
0.6-0.7	25
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8539	High Similarity	NPD1695	Approved
0.8	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6371	Approved
0.729	Intermediate Similarity	NPD6053	Discontinued
0.7234	Intermediate Similarity	NPD4249	Approved
0.7158	Intermediate Similarity	NPD4250	Approved
0.7158	Intermediate Similarity	NPD4251	Approved
0.7128	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5362	Discontinued
0.6939	Remote Similarity	NPD5785	Approved
0.6882	Remote Similarity	NPD5369	Approved
0.6809	Remote Similarity	NPD6435	Approved
0.6774	Remote Similarity	NPD4819	Approved
0.6774	Remote Similarity	NPD4821	Approved
0.6774	Remote Similarity	NPD4820	Approved
0.6774	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4822	Approved
0.6771	Remote Similarity	NPD5363	Approved
0.6768	Remote Similarity	NPD46	Approved
0.6768	Remote Similarity	NPD6698	Approved
0.6733	Remote Similarity	NPD5282	Discontinued
0.6729	Remote Similarity	NPD6008	Approved
0.6632	Remote Similarity	NPD4269	Approved
0.6632	Remote Similarity	NPD4270	Approved
0.6596	Remote Similarity	NPD5368	Approved
0.6562	Remote Similarity	NPD5332	Approved
0.6562	Remote Similarity	NPD7154	Phase 3
0.6562	Remote Similarity	NPD5331	Approved
0.6559	Remote Similarity	NPD4268	Approved
0.6559	Remote Similarity	NPD4271	Approved
0.6531	Remote Similarity	NPD5786	Approved
0.6526	Remote Similarity	NPD4790	Discontinued
0.6505	Remote Similarity	NPD5695	Phase 3
0.6476	Remote Similarity	NPD5696	Approved
0.6476	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD6399	Phase 3
0.6436	Remote Similarity	NPD7838	Discovery
0.6421	Remote Similarity	NPD4252	Approved
0.6415	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD7640	Approved
0.6381	Remote Similarity	NPD6083	Phase 2
0.6381	Remote Similarity	NPD6084	Phase 2
0.6373	Remote Similarity	NPD8034	Phase 2
0.6373	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD5697	Approved
0.6316	Remote Similarity	NPD8133	Approved
0.6306	Remote Similarity	NPD6686	Approved
0.6306	Remote Similarity	NPD7320	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6283	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7507	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6263	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6224	Remote Similarity	NPD4788	Approved
0.6216	Remote Similarity	NPD5701	Approved
0.6214	Remote Similarity	NPD5281	Approved
0.6214	Remote Similarity	NPD5693	Phase 1
0.6214	Remote Similarity	NPD5284	Approved
0.6214	Remote Similarity	NPD7983	Approved
0.6211	Remote Similarity	NPD4238	Approved
0.6211	Remote Similarity	NPD4802	Phase 2
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7492	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.619	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4632	Approved
0.6168	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4225	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD7115	Discovery
0.6154	Remote Similarity	NPD5779	Approved
0.6148	Remote Similarity	NPD6616	Approved
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD6869	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6134	Remote Similarity	NPD6319	Approved
0.6129	Remote Similarity	NPD7319	Approved
0.6122	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3198	Approved
0.6117	Remote Similarity	NPD5207	Approved
0.6098	Remote Similarity	NPD7078	Approved
0.6087	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD8297	Approved
0.6083	Remote Similarity	NPD6015	Approved
0.6083	Remote Similarity	NPD6016	Approved
0.6078	Remote Similarity	NPD6903	Approved
0.6071	Remote Similarity	NPD6412	Phase 2
0.6058	Remote Similarity	NPD7637	Suspended
0.6055	Remote Similarity	NPD5344	Discontinued
0.6055	Remote Similarity	NPD1700	Approved
0.6053	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7736	Approved
0.604	Remote Similarity	NPD5330	Approved
0.604	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD6409	Approved
0.604	Remote Similarity	NPD7521	Approved
0.604	Remote Similarity	NPD7146	Approved
0.604	Remote Similarity	NPD6684	Approved
0.6038	Remote Similarity	NPD5210	Approved
0.6038	Remote Similarity	NPD4629	Approved
0.6033	Remote Similarity	NPD6370	Approved
0.6033	Remote Similarity	NPD5988	Approved
0.6019	Remote Similarity	NPD4753	Phase 2
0.6017	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD7632	Discontinued
0.5968	Remote Similarity	NPD8293	Discontinued
0.5966	Remote Similarity	NPD7328	Approved
0.5966	Remote Similarity	NPD7327	Approved
0.5965	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5286	Approved
0.5963	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD6648	Approved
0.5963	Remote Similarity	NPD5285	Approved
0.595	Remote Similarity	NPD5983	Phase 2
0.595	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8033	Approved
0.5943	Remote Similarity	NPD6001	Approved
0.5941	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6274	Approved
0.5926	Remote Similarity	NPD4755	Approved
0.5922	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7516	Approved
0.59	Remote Similarity	NPD6695	Phase 3
0.5895	Remote Similarity	NPD3702	Approved
0.5893	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5141	Approved
0.5877	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD8377	Approved
0.5868	Remote Similarity	NPD8294	Approved
0.5865	Remote Similarity	NPD6101	Approved
0.5865	Remote Similarity	NPD6904	Approved
0.5865	Remote Similarity	NPD6051	Approved
0.5865	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6080	Approved
0.5865	Remote Similarity	NPD6673	Approved
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5226	Approved
0.5856	Remote Similarity	NPD4633	Approved
0.5856	Remote Similarity	NPD5224	Approved
0.5856	Remote Similarity	NPD5225	Approved
0.5854	Remote Similarity	NPD7604	Phase 2
0.5849	Remote Similarity	NPD4202	Approved
0.5842	Remote Similarity	NPD3133	Approved
0.5842	Remote Similarity	NPD3666	Approved
0.5842	Remote Similarity	NPD3665	Phase 1
0.582	Remote Similarity	NPD8516	Approved
0.582	Remote Similarity	NPD8380	Approved
0.582	Remote Similarity	NPD8378	Approved
0.582	Remote Similarity	NPD8513	Phase 3
0.582	Remote Similarity	NPD8379	Approved
0.582	Remote Similarity	NPD7503	Approved
0.582	Remote Similarity	NPD8515	Approved
0.582	Remote Similarity	NPD8517	Approved
0.582	Remote Similarity	NPD8335	Approved
0.582	Remote Similarity	NPD8296	Approved
0.5818	Remote Similarity	NPD4700	Approved
0.581	Remote Similarity	NPD5692	Phase 3
0.5804	Remote Similarity	NPD5174	Approved
0.5804	Remote Similarity	NPD5175	Approved
0.58	Remote Similarity	NPD4223	Phase 3
0.58	Remote Similarity	NPD4221	Approved
0.58	Remote Similarity	NPD5209	Approved
0.5789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6685	Approved
0.5785	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD7101	Approved
0.5776	Remote Similarity	NPD4634	Approved
0.5769	Remote Similarity	NPD6672	Approved
0.5769	Remote Similarity	NPD5737	Approved
0.5769	Remote Similarity	NPD5208	Approved
0.5766	Remote Similarity	NPD5223	Approved
0.576	Remote Similarity	NPD6336	Discontinued
0.5755	Remote Similarity	NPD6411	Approved
0.5755	Remote Similarity	NPD5694	Approved
0.5755	Remote Similarity	NPD6050	Approved
0.575	Remote Similarity	NPD6317	Approved
0.5736	Remote Similarity	NPD6845	Suspended
0.5728	Remote Similarity	NPD5690	Phase 2

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