NPASS Compound

Structure

CID245948 OpenBabel06191716042D 31 34 0 0 1 0 0 0 0 0999 V2000 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 10 1 0 0 0 0 5 17 2 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 23 1 0 0 0 0 9 30 1 0 0 0 0 9 31 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 8 1 6 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 21 1 0 0 0 0 17 28 1 0 0 0 0 18 10 1 1 0 0 0 18 19 1 0 0 0 0 19 22 1 1 0 0 0 20 24 1 1 0 0 0 21 29 1 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.14
Volume:	415.499
LogP:	1.238
LogD:	1.247
LogS:	-3.37
# Rotatable Bonds:	6
TPSA:	123.91
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	3.778
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.625
MDCK Permeability:	1.4302177987701725e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	93.59146118164062%
Volume Distribution (VD):	0.915
Pgp-substrate:	6.522782325744629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.732
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.897

ADMET: Excretion

Clearance (CL):	5.105
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.605
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.037
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.334

Download Data

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

Natural Product: NPC245948

Natural Product ID:	NPC245948
*Common Name:**	(5R,6R,7R,8R)-8-Hydroxy-7-(Hydroxymethyl)-5-(3,4,5-Trimethoxyphenyl)-5,6,7,8-Tetrahydrobenzo[F][1,3]Benzodioxole-6-Carboxylic Acid
IUPAC Name:	(5R,6R,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid
Synonyms:
Standard InCHIKey:	XRBSKUSTLXISAB-XVVDYKMHSA-N
Standard InCHI:	InChI=1S/C22H24O9/c1-27-16-4-10(5-17(28-2)21(16)29-3)18-11-6-14-15(31-9-30-14)7-12(11)20(24)13(8-23)19(18)22(25)26/h4-7,13,18-20,23-24H,8-9H2,1-3H3,(H,25,26)/t13-,18+,19-,20-/m0/s1
SMILES:	OC[C@@H]1[C@@H](O)c2cc3OCOc3cc2[C@H]([C@H]1C(=O)O)c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL32955
PubChem CID:	134632
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans [CHEMONTID:0003426] 9,9p-dihydroxyaryltetralin lignans

*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
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94598-9]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2225/vol5-issue3-fulltext-4]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325242]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088440]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713420]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15009205]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038560]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25323720]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	rhizomes	Liaoning province, China	2011-SEP	PMID[25927664]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26731565]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31419126]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21938	Coleus carnosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16829	Dunaliella acidophila	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11677	Lactobacillus acidophilus	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17718	Artemisia schmidtiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19057	Lentinellus omphalodes	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18575	Ochtodes crockeri	Species	Rhizophyllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19189	Brickellia pendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18173	Pyrocystis lunula	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3050	Cladonia pseudodidyma	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15608	Tanacetum santolina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9535	Cortinarius basirubescens	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18520	Helipterum strictum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12801	Aglaia meridionalis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17275	Chamaemelum scariosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18792	Crotalaria lechnaultii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7807	Polyporus sulphureus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17709	Timonius kaniensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18061	Anacystis cyanea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12282	Parmelia conspersa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3746	Hesperocyparis nevadensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18847	Copaifera paupera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17190	Senecio erraticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18242	Gleichenia glauca	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12072	Escallonia philippiana	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13594	Hippocratea indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17596	Ficus maxima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17068	Talaromyces wortmanni	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18377	Chaetomium retardatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11603	Lathyrus macrorrhizus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10712	Tabebuia rosea	Species	Bignoniaceae	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
GI50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	<	10.0	nM	PMID[486868]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	=	55000.0	nM	PMID[486868]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	40000.0	nM	PMID[486868]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	>	100000.0	nM	PMID[486868]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	50000.0	nM	PMID[486868]
NPT386	Cell Line	KM12	Homo sapiens	GI50	<	10.0	nM	PMID[486868]

☑ 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 NPC245948 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	333
0.1-0.2	1347
0.2-0.3	3039
0.3-0.4	6772
0.4-0.5	10997
0.5-0.6	4740
0.6-0.7	6936
0.7-0.8	7724
0.8-0.85	592
0.85-0.9	184
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC32373
0.9797	High Similarity	NPC237946
0.9732	High Similarity	NPC19947
0.9732	High Similarity	NPC207584
0.9603	High Similarity	NPC150943
0.9603	High Similarity	NPC268718
0.9603	High Similarity	NPC119910
0.9603	High Similarity	NPC91634
0.9539	High Similarity	NPC288149
0.9474	High Similarity	NPC96593
0.9463	High Similarity	NPC178574
0.9463	High Similarity	NPC65591
0.9459	High Similarity	NPC210642
0.9459	High Similarity	NPC13985
0.9416	High Similarity	NPC116759
0.9416	High Similarity	NPC14294
0.9412	High Similarity	NPC100465
0.9412	High Similarity	NPC152424
0.9342	High Similarity	NPC181168
0.9342	High Similarity	NPC115281
0.9342	High Similarity	NPC163527
0.9286	High Similarity	NPC115624
0.9272	High Similarity	NPC103197
0.9272	High Similarity	NPC273578
0.9272	High Similarity	NPC30009
0.9262	High Similarity	NPC149505
0.9257	High Similarity	NPC304821
0.9236	High Similarity	NPC185498
0.9231	High Similarity	NPC222531
0.9189	High Similarity	NPC304687
0.9189	High Similarity	NPC101755
0.9189	High Similarity	NPC104024
0.9189	High Similarity	NPC65574
0.9189	High Similarity	NPC80230
0.9172	High Similarity	NPC306475
0.9139	High Similarity	NPC56184
0.9133	High Similarity	NPC24425
0.9119	High Similarity	NPC179240
0.9067	High Similarity	NPC177476
0.9067	High Similarity	NPC477698
0.9067	High Similarity	NPC262455
0.902	High Similarity	NPC136757
0.9	High Similarity	NPC316676
0.9	High Similarity	NPC325720
0.8961	High Similarity	NPC238834
0.8947	High Similarity	NPC164082
0.8947	High Similarity	NPC303519
0.894	High Similarity	NPC474965
0.894	High Similarity	NPC174512
0.894	High Similarity	NPC477695
0.894	High Similarity	NPC293757
0.894	High Similarity	NPC668
0.8931	High Similarity	NPC174734
0.8931	High Similarity	NPC474042
0.8896	High Similarity	NPC473425
0.8889	High Similarity	NPC477699
0.8882	High Similarity	NPC473989
0.8875	High Similarity	NPC471180
0.8874	High Similarity	NPC40654
0.8874	High Similarity	NPC262804
0.8854	High Similarity	NPC474770
0.8851	High Similarity	NPC151423
0.8851	High Similarity	NPC287124
0.8851	High Similarity	NPC40237
0.8831	High Similarity	NPC24562
0.8831	High Similarity	NPC474606
0.8824	High Similarity	NPC475756
0.8824	High Similarity	NPC477700
0.882	High Similarity	NPC117911
0.8816	High Similarity	NPC216223
0.8816	High Similarity	NPC145569
0.8792	High Similarity	NPC470811
0.8792	High Similarity	NPC477696
0.8792	High Similarity	NPC474288
0.8792	High Similarity	NPC324962
0.8792	High Similarity	NPC477697
0.8774	High Similarity	NPC178195
0.8774	High Similarity	NPC348849
0.8774	High Similarity	NPC312763
0.8766	High Similarity	NPC471154
0.8766	High Similarity	NPC476434
0.8758	High Similarity	NPC229882
0.8758	High Similarity	NPC158635
0.8758	High Similarity	NPC311912
0.8742	High Similarity	NPC321696
0.8742	High Similarity	NPC321958
0.8742	High Similarity	NPC3982
0.8742	High Similarity	NPC212890
0.8733	High Similarity	NPC475000
0.8733	High Similarity	NPC166884
0.8733	High Similarity	NPC141569
0.8733	High Similarity	NPC92693
0.8733	High Similarity	NPC477701
0.8733	High Similarity	NPC218841
0.8725	High Similarity	NPC210354
0.8725	High Similarity	NPC229172
0.8725	High Similarity	NPC191231
0.8725	High Similarity	NPC103637
0.8725	High Similarity	NPC52664
0.8725	High Similarity	NPC176586
0.8725	High Similarity	NPC230538
0.8725	High Similarity	NPC36531
0.8712	High Similarity	NPC471181
0.871	High Similarity	NPC115466
0.871	High Similarity	NPC61604
0.871	High Similarity	NPC245615
0.871	High Similarity	NPC474514
0.871	High Similarity	NPC299706
0.8707	High Similarity	NPC196420
0.8704	High Similarity	NPC88557
0.8701	High Similarity	NPC32079
0.8699	High Similarity	NPC44245
0.8699	High Similarity	NPC72796
0.8696	High Similarity	NPC83049
0.8696	High Similarity	NPC118162
0.8696	High Similarity	NPC320471
0.8693	High Similarity	NPC125570
0.8688	High Similarity	NPC475865
0.8675	High Similarity	NPC477702
0.8675	High Similarity	NPC318286
0.8675	High Similarity	NPC327651
0.8675	High Similarity	NPC475868
0.8671	High Similarity	NPC173726
0.8671	High Similarity	NPC241600
0.8671	High Similarity	NPC474043
0.8667	High Similarity	NPC218510
0.8667	High Similarity	NPC106920
0.8667	High Similarity	NPC76415
0.8667	High Similarity	NPC273657
0.8662	High Similarity	NPC29727
0.8662	High Similarity	NPC473323
0.8645	High Similarity	NPC302610
0.8642	High Similarity	NPC79322
0.8636	High Similarity	NPC260781
0.8636	High Similarity	NPC218041
0.8636	High Similarity	NPC469706
0.8636	High Similarity	NPC182368
0.8636	High Similarity	NPC185955
0.8636	High Similarity	NPC145979
0.8636	High Similarity	NPC9933
0.8636	High Similarity	NPC225815
0.8636	High Similarity	NPC469707
0.8636	High Similarity	NPC214326
0.8625	High Similarity	NPC116838
0.8625	High Similarity	NPC22130
0.8618	High Similarity	NPC33832
0.8618	High Similarity	NPC193779
0.8616	High Similarity	NPC63061
0.8616	High Similarity	NPC470637
0.8609	High Similarity	NPC326144
0.8609	High Similarity	NPC239254
0.8609	High Similarity	NPC191158
0.8609	High Similarity	NPC172171
0.8609	High Similarity	NPC177644
0.8599	High Similarity	NPC234730
0.8599	High Similarity	NPC38699
0.8599	High Similarity	NPC476065
0.859	High Similarity	NPC217708
0.859	High Similarity	NPC16791
0.859	High Similarity	NPC308739
0.859	High Similarity	NPC297271
0.859	High Similarity	NPC77237
0.859	High Similarity	NPC126405
0.859	High Similarity	NPC53669
0.859	High Similarity	NPC473236
0.8581	High Similarity	NPC474039
0.8581	High Similarity	NPC224472
0.8571	High Similarity	NPC469475
0.8571	High Similarity	NPC150534
0.8571	High Similarity	NPC211386
0.8571	High Similarity	NPC469518
0.8562	High Similarity	NPC196937
0.8562	High Similarity	NPC191352
0.8562	High Similarity	NPC319749
0.8562	High Similarity	NPC209411
0.8562	High Similarity	NPC258322
0.8562	High Similarity	NPC239890
0.8554	High Similarity	NPC196771
0.8553	High Similarity	NPC125713
0.8553	High Similarity	NPC197352
0.8553	High Similarity	NPC166506
0.8553	High Similarity	NPC230531
0.8553	High Similarity	NPC110763
0.8553	High Similarity	NPC325122
0.8553	High Similarity	NPC474158
0.8553	High Similarity	NPC189239
0.8553	High Similarity	NPC215400
0.8544	High Similarity	NPC163635
0.8544	High Similarity	NPC477380
0.8544	High Similarity	NPC478055
0.8537	High Similarity	NPC477883
0.8535	High Similarity	NPC198461
0.8533	High Similarity	NPC100675
0.8533	High Similarity	NPC29599
0.8533	High Similarity	NPC470991
0.8523	High Similarity	NPC114171
0.8523	High Similarity	NPC6300
0.8523	High Similarity	NPC230124
0.8516	High Similarity	NPC316989
0.8514	High Similarity	NPC11453

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 NPC245948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	882
0.2-0.3	1687
0.3-0.4	2584
0.4-0.5	1992
0.5-0.6	1010
0.6-0.7	566
0.7-0.8	131
0.8-0.85	6
0.85-0.9	4
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD37	Approved
0.9797	High Similarity	NPD4967	Phase 2
0.9797	High Similarity	NPD4966	Approved
0.9797	High Similarity	NPD4965	Approved
0.9536	High Similarity	NPD6234	Discontinued
0.9236	High Similarity	NPD7228	Approved
0.8889	High Similarity	NPD7240	Approved
0.8797	High Similarity	NPD7199	Phase 2
0.8571	High Similarity	NPD7184	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6232	Discontinued
0.8269	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.8129	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8056	Intermediate Similarity	NPD7680	Approved
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3027	Phase 3
0.7821	Intermediate Similarity	NPD6674	Discontinued
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7784	Intermediate Similarity	NPD8127	Discontinued
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.7746	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3705	Approved
0.7738	Intermediate Similarity	NPD7229	Phase 3
0.7719	Intermediate Similarity	NPD7054	Approved
0.7688	Intermediate Similarity	NPD2534	Approved
0.7688	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD2533	Approved
0.7674	Intermediate Similarity	NPD7472	Approved
0.7654	Intermediate Similarity	NPD1653	Approved
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7636	Intermediate Similarity	NPD8455	Phase 2
0.7619	Intermediate Similarity	NPD5494	Approved
0.759	Intermediate Similarity	NPD3817	Phase 2
0.7586	Intermediate Similarity	NPD7685	Pre-registration
0.7584	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1934	Approved
0.7561	Intermediate Similarity	NPD7028	Phase 2
0.7547	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4110	Phase 3
0.7544	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6166	Phase 2
0.7543	Intermediate Similarity	NPD7808	Phase 3
0.7532	Intermediate Similarity	NPD3620	Phase 2
0.7532	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1613	Approved
0.7532	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7819	Suspended
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2438	Suspended
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7468	Intermediate Similarity	NPD7266	Discontinued
0.7467	Intermediate Similarity	NPD1283	Approved
0.744	Intermediate Similarity	NPD3882	Suspended
0.7438	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2801	Approved
0.7421	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7458	Discontinued
0.7389	Intermediate Similarity	NPD7097	Phase 1
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7368	Intermediate Similarity	NPD6959	Discontinued
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7349	Intermediate Similarity	NPD4380	Phase 2
0.7344	Intermediate Similarity	NPD7827	Phase 1
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7329	Intermediate Similarity	NPD3750	Approved
0.732	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6273	Approved
0.7314	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.7308	Intermediate Similarity	NPD2979	Phase 3
0.7308	Intermediate Similarity	NPD4140	Approved
0.7297	Intermediate Similarity	NPD1357	Approved
0.7296	Intermediate Similarity	NPD6100	Approved
0.7296	Intermediate Similarity	NPD6099	Approved
0.7294	Intermediate Similarity	NPD7075	Discontinued
0.729	Intermediate Similarity	NPD6798	Discontinued
0.729	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5402	Approved
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1281	Approved
0.7262	Intermediate Similarity	NPD6801	Discontinued
0.7261	Intermediate Similarity	NPD230	Phase 1
0.7255	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6004	Phase 3
0.725	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6002	Phase 3
0.725	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5763	Approved
0.725	Intermediate Similarity	NPD6005	Phase 3
0.725	Intermediate Similarity	NPD5762	Approved
0.7244	Intermediate Similarity	NPD6233	Phase 2
0.7222	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7202	Intermediate Similarity	NPD7411	Suspended
0.7193	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2935	Discontinued
0.7186	Intermediate Similarity	NPD3226	Approved
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3764	Approved
0.7176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2982	Phase 2
0.7171	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD5006	Approved
0.7135	Intermediate Similarity	NPD7768	Phase 2
0.7134	Intermediate Similarity	NPD8032	Phase 2
0.7134	Intermediate Similarity	NPD6663	Approved
0.7126	Intermediate Similarity	NPD5710	Approved
0.7126	Intermediate Similarity	NPD5711	Approved
0.7125	Intermediate Similarity	NPD3748	Approved
0.7125	Intermediate Similarity	NPD7033	Discontinued
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.712	Intermediate Similarity	NPD7296	Approved
0.7117	Intermediate Similarity	NPD8166	Discontinued
0.7117	Intermediate Similarity	NPD7003	Approved
0.7115	Intermediate Similarity	NPD4625	Phase 3
0.711	Intermediate Similarity	NPD6746	Phase 2
0.7105	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7105	Intermediate Similarity	NPD2981	Phase 2
0.7097	Intermediate Similarity	NPD5736	Approved
0.7093	Intermediate Similarity	NPD3749	Approved
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7091	Intermediate Similarity	NPD1511	Approved
0.7086	Intermediate Similarity	NPD5242	Approved
0.7083	Intermediate Similarity	NPD4005	Discontinued
0.7078	Intermediate Similarity	NPD2797	Approved
0.7076	Intermediate Similarity	NPD5353	Approved
0.707	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1651	Approved
0.7066	Intermediate Similarity	NPD5403	Approved
0.7055	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD919	Approved
0.7048	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3657	Discovery
0.7044	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5124	Phase 1
0.7041	Intermediate Similarity	NPD6599	Discontinued
0.7039	Intermediate Similarity	NPD1610	Phase 2
0.7037	Intermediate Similarity	NPD6780	Approved
0.7037	Intermediate Similarity	NPD6781	Approved
0.7037	Intermediate Similarity	NPD6779	Approved
0.7037	Intermediate Similarity	NPD6777	Approved
0.7037	Intermediate Similarity	NPD6776	Approved
0.7037	Intermediate Similarity	NPD6778	Approved
0.7037	Intermediate Similarity	NPD6782	Approved
0.7021	Intermediate Similarity	NPD4420	Approved
0.702	Intermediate Similarity	NPD5125	Phase 3
0.702	Intermediate Similarity	NPD4626	Approved
0.702	Intermediate Similarity	NPD5126	Approved
0.7019	Intermediate Similarity	NPD1510	Phase 2
0.7006	Intermediate Similarity	NPD7095	Approved
0.7006	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1512	Approved
0.7	Intermediate Similarity	NPD6653	Approved
0.6989	Remote Similarity	NPD3926	Phase 2
0.6988	Remote Similarity	NPD6799	Approved
0.6987	Remote Similarity	NPD2861	Phase 2
0.6975	Remote Similarity	NPD2531	Phase 2
0.697	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6823	Phase 2
0.6962	Remote Similarity	NPD3268	Approved
0.6961	Remote Similarity	NPD7549	Discontinued
0.6949	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4749	Approved
0.6948	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5401	Approved
0.6939	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7783	Phase 2
0.6937	Remote Similarity	NPD1933	Approved
0.6937	Remote Similarity	NPD5735	Approved
0.6937	Remote Similarity	NPD447	Suspended
0.6933	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2346	Discontinued

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