NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	207.09
Volume:	208.521
LogP:	0.441
LogD:	1.332
LogS:	-0.394
# Rotatable Bonds:	1
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	2.182
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.569
MDCK Permeability:	9.72531324805459e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.205

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965
Plasma Protein Binding (PPB):	53.741668701171875%
Volume Distribution (VD):	1.276
Pgp-substrate:	46.03923416137695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.424
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.408
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	6.676
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.244
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.129
Carcinogencity:	0.039
Eye Corrosion:	0.012
Eye Irritation:	0.54
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC135006

Natural Product ID:	NPC135006
*Common Name:**	Thalifoline
IUPAC Name:	7-hydroxy-6-methoxy-2-methyl-3,4-dihydroisoquinolin-1-one
Synonyms:	Thalifoline
Standard InCHIKey:	WPKMGEQXTYQXGI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H13NO3/c1-12-4-3-7-5-10(15-2)9(13)6-8(7)11(12)14/h5-6,13H,3-4H2,1-2H3
SMILES:	COc1cc2CCN(C(=O)c2cc1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813177
PubChem CID:	89048
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002054] Isoquinolones 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
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[10075775]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479331]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473438]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15387664]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21094631]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26238319]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8281582]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[9428162]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11635.1	Thalictrum minus var. adiantifolium	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11635.1	Thalictrum minus var. adiantifolium	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3790	Cryptocarya longifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12223	Stellaria media	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19709	Pseudocyphellaria australiensis	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8172	Emericellopsis minima	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17630	Helenium integrifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18533	Delisea elegans	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17499	Bursera kerberi	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20526	Menispermum dauricum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16325	Sideritis dasygnaphala	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19170	Lasianthaea podocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15127	Senecio congestus	Species	Asteraceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	1000000.0	nM	PMID[525399]

☑ 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 NPC135006 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	251
0.1-0.2	1690
0.2-0.3	6548
0.3-0.4	11226
0.4-0.5	4305
0.5-0.6	11370
0.6-0.7	6630
0.7-0.8	640
0.8-0.85	31
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.953	High Similarity	NPC119669
0.8591	High Similarity	NPC131204
0.8591	High Similarity	NPC301050
0.8431	Intermediate Similarity	NPC138438
0.8431	Intermediate Similarity	NPC908
0.8355	Intermediate Similarity	NPC231572
0.8344	Intermediate Similarity	NPC153631
0.8249	Intermediate Similarity	NPC24228
0.8225	Intermediate Similarity	NPC20395
0.8199	Intermediate Similarity	NPC470708
0.8176	Intermediate Similarity	NPC222524
0.8176	Intermediate Similarity	NPC469539
0.8176	Intermediate Similarity	NPC469540
0.8095	Intermediate Similarity	NPC86469
0.8089	Intermediate Similarity	NPC294249
0.8089	Intermediate Similarity	NPC125852
0.8067	Intermediate Similarity	NPC160193
0.805	Intermediate Similarity	NPC179825
0.805	Intermediate Similarity	NPC191376
0.805	Intermediate Similarity	NPC321505
0.8	Intermediate Similarity	NPC428
0.8	Intermediate Similarity	NPC147390
0.8	Intermediate Similarity	NPC246587
0.8	Intermediate Similarity	NPC67978
0.8	Intermediate Similarity	NPC24233
0.8	Intermediate Similarity	NPC135538
0.8	Intermediate Similarity	NPC303581
0.8	Intermediate Similarity	NPC476571
0.7956	Intermediate Similarity	NPC207239
0.7955	Intermediate Similarity	NPC162694
0.795	Intermediate Similarity	NPC470088
0.795	Intermediate Similarity	NPC477565
0.795	Intermediate Similarity	NPC103379
0.7925	Intermediate Similarity	NPC185838
0.7907	Intermediate Similarity	NPC308267
0.7901	Intermediate Similarity	NPC88249
0.7901	Intermediate Similarity	NPC97221
0.7901	Intermediate Similarity	NPC220858
0.7901	Intermediate Similarity	NPC151895
0.7901	Intermediate Similarity	NPC192768
0.7877	Intermediate Similarity	NPC254957
0.7857	Intermediate Similarity	NPC476569
0.7857	Intermediate Similarity	NPC267414
0.7853	Intermediate Similarity	NPC169387
0.7853	Intermediate Similarity	NPC477259
0.7841	Intermediate Similarity	NPC116007
0.7826	Intermediate Similarity	NPC476151
0.7815	Intermediate Similarity	NPC16651
0.7815	Intermediate Similarity	NPC32163
0.7812	Intermediate Similarity	NPC469978
0.7811	Intermediate Similarity	NPC35345
0.7809	Intermediate Similarity	NPC208890
0.7805	Intermediate Similarity	NPC133011
0.7805	Intermediate Similarity	NPC82285
0.7802	Intermediate Similarity	NPC71124
0.7792	Intermediate Similarity	NPC160692
0.7792	Intermediate Similarity	NPC266425
0.7778	Intermediate Similarity	NPC470324
0.7778	Intermediate Similarity	NPC153644
0.7771	Intermediate Similarity	NPC99723
0.7765	Intermediate Similarity	NPC206941
0.7756	Intermediate Similarity	NPC7018
0.7744	Intermediate Similarity	NPC277669
0.7744	Intermediate Similarity	NPC76213
0.774	Intermediate Similarity	NPC83511
0.7727	Intermediate Similarity	NPC298339
0.7722	Intermediate Similarity	NPC226708
0.772	Intermediate Similarity	NPC82056
0.7714	Intermediate Similarity	NPC121400
0.7713	Intermediate Similarity	NPC100573
0.7713	Intermediate Similarity	NPC207873
0.7711	Intermediate Similarity	NPC110416
0.7711	Intermediate Similarity	NPC207757
0.7711	Intermediate Similarity	NPC276588
0.7711	Intermediate Similarity	NPC54379
0.7711	Intermediate Similarity	NPC295691
0.7711	Intermediate Similarity	NPC469817
0.7711	Intermediate Similarity	NPC172765
0.7711	Intermediate Similarity	NPC127674
0.7711	Intermediate Similarity	NPC39701
0.7711	Intermediate Similarity	NPC278799
0.7711	Intermediate Similarity	NPC189266
0.7711	Intermediate Similarity	NPC2413
0.7711	Intermediate Similarity	NPC5238
0.7711	Intermediate Similarity	NPC204828
0.7711	Intermediate Similarity	NPC184026
0.7711	Intermediate Similarity	NPC249797
0.7711	Intermediate Similarity	NPC193949
0.767	Intermediate Similarity	NPC27887
0.7665	Intermediate Similarity	NPC147091
0.7665	Intermediate Similarity	NPC57512
0.7663	Intermediate Similarity	NPC5374
0.7651	Intermediate Similarity	NPC477564
0.7651	Intermediate Similarity	NPC2295
0.7636	Intermediate Similarity	NPC476579
0.7633	Intermediate Similarity	NPC226428
0.7622	Intermediate Similarity	NPC207824
0.7622	Intermediate Similarity	NPC60538
0.7617	Intermediate Similarity	NPC38964
0.7616	Intermediate Similarity	NPC30216
0.761	Intermediate Similarity	NPC314682
0.7596	Intermediate Similarity	NPC477258
0.7596	Intermediate Similarity	NPC33256
0.7595	Intermediate Similarity	NPC253429
0.7594	Intermediate Similarity	NPC207971
0.759	Intermediate Similarity	NPC476580
0.759	Intermediate Similarity	NPC37272
0.759	Intermediate Similarity	NPC223124
0.7582	Intermediate Similarity	NPC117237
0.7582	Intermediate Similarity	NPC94499
0.7582	Intermediate Similarity	NPC203719
0.7578	Intermediate Similarity	NPC84273
0.7576	Intermediate Similarity	NPC274026
0.7574	Intermediate Similarity	NPC111485
0.7564	Intermediate Similarity	NPC50763
0.7562	Intermediate Similarity	NPC188163
0.7562	Intermediate Similarity	NPC213206
0.7562	Intermediate Similarity	NPC474915
0.7562	Intermediate Similarity	NPC328750
0.7557	Intermediate Similarity	NPC35680
0.7553	Intermediate Similarity	NPC268077
0.7548	Intermediate Similarity	NPC66905
0.7541	Intermediate Similarity	NPC469816
0.7541	Intermediate Similarity	NPC469815
0.7531	Intermediate Similarity	NPC169214
0.7531	Intermediate Similarity	NPC192597
0.7531	Intermediate Similarity	NPC229218
0.7531	Intermediate Similarity	NPC141817
0.7531	Intermediate Similarity	NPC176030
0.7529	Intermediate Similarity	NPC249274
0.7529	Intermediate Similarity	NPC166014
0.7529	Intermediate Similarity	NPC27410
0.7529	Intermediate Similarity	NPC205167
0.7514	Intermediate Similarity	NPC21885
0.75	Intermediate Similarity	NPC255607
0.75	Intermediate Similarity	NPC3375
0.75	Intermediate Similarity	NPC231198
0.7486	Intermediate Similarity	NPC227683
0.7485	Intermediate Similarity	NPC60186
0.7484	Intermediate Similarity	NPC225745
0.7484	Intermediate Similarity	NPC252107
0.7472	Intermediate Similarity	NPC32154
0.747	Intermediate Similarity	NPC223125
0.7469	Intermediate Similarity	NPC476567
0.7469	Intermediate Similarity	NPC128019
0.7469	Intermediate Similarity	NPC136860
0.7468	Intermediate Similarity	NPC172403
0.7459	Intermediate Similarity	NPC124626
0.7456	Intermediate Similarity	NPC186063
0.7452	Intermediate Similarity	NPC111888
0.7443	Intermediate Similarity	NPC256935
0.7442	Intermediate Similarity	NPC59567
0.7442	Intermediate Similarity	NPC324144
0.7436	Intermediate Similarity	NPC298268
0.7427	Intermediate Similarity	NPC158900
0.7421	Intermediate Similarity	NPC99078
0.7421	Intermediate Similarity	NPC208760
0.7421	Intermediate Similarity	NPC139519
0.7419	Intermediate Similarity	NPC293624
0.7414	Intermediate Similarity	NPC284842
0.7412	Intermediate Similarity	NPC475326
0.7405	Intermediate Similarity	NPC167096
0.7405	Intermediate Similarity	NPC283823
0.7405	Intermediate Similarity	NPC125924
0.7405	Intermediate Similarity	NPC159418
0.7403	Intermediate Similarity	NPC218323
0.7399	Intermediate Similarity	NPC238530
0.7399	Intermediate Similarity	NPC13504
0.7399	Intermediate Similarity	NPC4138
0.7399	Intermediate Similarity	NPC136508
0.7399	Intermediate Similarity	NPC276944
0.7399	Intermediate Similarity	NPC78222
0.7399	Intermediate Similarity	NPC24465
0.7399	Intermediate Similarity	NPC253043
0.7399	Intermediate Similarity	NPC477563
0.7399	Intermediate Similarity	NPC306843
0.7399	Intermediate Similarity	NPC232514
0.7399	Intermediate Similarity	NPC306669
0.7399	Intermediate Similarity	NPC212794
0.7399	Intermediate Similarity	NPC121275
0.7399	Intermediate Similarity	NPC284183
0.7399	Intermediate Similarity	NPC196447
0.7399	Intermediate Similarity	NPC96603
0.7394	Intermediate Similarity	NPC73416
0.7394	Intermediate Similarity	NPC160777
0.7389	Intermediate Similarity	NPC93882
0.7389	Intermediate Similarity	NPC300020
0.7389	Intermediate Similarity	NPC130595
0.7389	Intermediate Similarity	NPC33338
0.7389	Intermediate Similarity	NPC302171
0.7385	Intermediate Similarity	NPC298449
0.7382	Intermediate Similarity	NPC308943
0.7381	Intermediate Similarity	NPC58661
0.7381	Intermediate Similarity	NPC270811
0.7381	Intermediate Similarity	NPC471073
0.7378	Intermediate Similarity	NPC130926
0.7375	Intermediate Similarity	NPC470707
0.7375	Intermediate Similarity	NPC220923
0.7368	Intermediate Similarity	NPC106786
0.7368	Intermediate Similarity	NPC163829

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 NPC135006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	732
0.2-0.3	1187
0.3-0.4	1931
0.4-0.5	2570
0.5-0.6	1877
0.6-0.7	585
0.7-0.8	78
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9272	High Similarity	NPD824	Approved
0.8599	High Similarity	NPD1337	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD5978	Approved
0.8272	Intermediate Similarity	NPD5977	Approved
0.8011	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6618	Phase 2
0.7975	Intermediate Similarity	NPD7110	Phase 1
0.7975	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3639	Approved
0.795	Intermediate Similarity	NPD3641	Approved
0.795	Intermediate Similarity	NPD3640	Phase 3
0.795	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD743	Approved
0.784	Intermediate Similarity	NPD1670	Discontinued
0.7805	Intermediate Similarity	NPD6876	Approved
0.7805	Intermediate Similarity	NPD6875	Approved
0.7778	Intermediate Similarity	NPD2898	Approved
0.7765	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6297	Approved
0.7727	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7291	Discontinued
0.7644	Intermediate Similarity	NPD5313	Approved
0.7644	Intermediate Similarity	NPD5312	Approved
0.7633	Intermediate Similarity	NPD1309	Phase 2
0.7633	Intermediate Similarity	NPD1307	Phase 2
0.7584	Intermediate Similarity	NPD6851	Approved
0.7584	Intermediate Similarity	NPD6853	Approved
0.7582	Intermediate Similarity	NPD9494	Approved
0.7562	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6386	Approved
0.7545	Intermediate Similarity	NPD6385	Approved
0.7541	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4166	Phase 2
0.7419	Intermediate Similarity	NPD5071	Phase 2
0.7389	Intermediate Similarity	NPD2674	Phase 3
0.7378	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5564	Approved
0.7358	Intermediate Similarity	NPD2492	Phase 1
0.7356	Intermediate Similarity	NPD4010	Discontinued
0.7342	Intermediate Similarity	NPD3140	Approved
0.7342	Intermediate Similarity	NPD3142	Approved
0.7337	Intermediate Similarity	NPD4772	Phase 2
0.7337	Intermediate Similarity	NPD4773	Phase 2
0.7314	Intermediate Similarity	NPD5242	Approved
0.7303	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6181	Discontinued
0.7289	Intermediate Similarity	NPD4584	Approved
0.7283	Intermediate Similarity	NPD2488	Approved
0.7283	Intermediate Similarity	NPD2490	Approved
0.7278	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6894	Phase 1
0.7263	Intermediate Similarity	NPD3448	Approved
0.7263	Intermediate Similarity	NPD2491	Approved
0.724	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7281	Phase 3
0.7238	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7280	Phase 3
0.7235	Intermediate Similarity	NPD6873	Phase 2
0.7215	Intermediate Similarity	NPD3145	Approved
0.7215	Intermediate Similarity	NPD3144	Approved
0.7213	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD3057	Approved
0.7169	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4420	Approved
0.7129	Intermediate Similarity	NPD6997	Phase 2
0.7126	Intermediate Similarity	NPD7833	Phase 2
0.7126	Intermediate Similarity	NPD7831	Phase 2
0.7126	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4017	Approved
0.711	Intermediate Similarity	NPD5353	Approved
0.711	Intermediate Similarity	NPD2563	Approved
0.711	Intermediate Similarity	NPD2560	Approved
0.7108	Intermediate Similarity	NPD5241	Discontinued
0.7107	Intermediate Similarity	NPD5718	Phase 2
0.7102	Intermediate Similarity	NPD6107	Approved
0.7101	Intermediate Similarity	NPD6031	Approved
0.7101	Intermediate Similarity	NPD6030	Approved
0.7095	Intermediate Similarity	NPD2822	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7177	Discontinued
0.7093	Intermediate Similarity	NPD7577	Discontinued
0.7092	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD8149	Discontinued
0.7083	Intermediate Similarity	NPD3533	Approved
0.7083	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2972	Approved
0.7074	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6071	Discontinued
0.7062	Intermediate Similarity	NPD5183	Approved
0.7062	Intermediate Similarity	NPD5186	Approved
0.7056	Intermediate Similarity	NPD6020	Phase 2
0.7048	Intermediate Similarity	NPD7048	Phase 3
0.7045	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3446	Phase 1
0.7037	Intermediate Similarity	NPD6834	Approved
0.7031	Intermediate Similarity	NPD2493	Approved
0.7031	Intermediate Similarity	NPD3452	Approved
0.7031	Intermediate Similarity	NPD2494	Approved
0.7031	Intermediate Similarity	NPD3450	Approved
0.7029	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3455	Phase 2
0.7012	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5967	Approved
0.6995	Remote Similarity	NPD5006	Approved
0.6995	Remote Similarity	NPD5005	Approved
0.6994	Remote Similarity	NPD7298	Approved
0.6987	Remote Similarity	NPD1755	Approved
0.6982	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3146	Approved
0.6981	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5457	Discontinued
0.6977	Remote Similarity	NPD2592	Discontinued
0.6968	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2904	Discontinued
0.694	Remote Similarity	NPD7038	Approved
0.694	Remote Similarity	NPD7039	Approved
0.6935	Remote Similarity	NPD7225	Discontinued
0.6923	Remote Similarity	NPD4583	Approved
0.6923	Remote Similarity	NPD5297	Approved
0.6923	Remote Similarity	NPD4582	Approved
0.6923	Remote Similarity	NPD2325	Approved
0.6919	Remote Similarity	NPD8054	Approved
0.6919	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2651	Approved
0.6919	Remote Similarity	NPD2649	Approved
0.6919	Remote Similarity	NPD8053	Approved
0.6915	Remote Similarity	NPD7047	Phase 3
0.6912	Remote Similarity	NPD7907	Approved
0.6906	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7693	Approved
0.6889	Remote Similarity	NPD27	Approved
0.6889	Remote Similarity	NPD2489	Approved
0.6886	Remote Similarity	NPD3060	Approved
0.6882	Remote Similarity	NPD1424	Approved
0.6879	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4004	Approved
0.6872	Remote Similarity	NPD4002	Approved
0.6865	Remote Similarity	NPD2971	Approved
0.6865	Remote Similarity	NPD2968	Approved
0.6851	Remote Similarity	NPD3366	Approved
0.6848	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4466	Phase 1
0.6839	Remote Similarity	NPD7810	Phase 3
0.6839	Remote Similarity	NPD7811	Phase 3
0.6833	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5025	Approved
0.6824	Remote Similarity	NPD2420	Approved
0.6824	Remote Similarity	NPD2421	Approved
0.6823	Remote Similarity	NPD2975	Approved
0.6823	Remote Similarity	NPD2973	Approved
0.6823	Remote Similarity	NPD2974	Approved
0.6818	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2821	Approved
0.6814	Remote Similarity	NPD4665	Approved
0.6814	Remote Similarity	NPD2899	Discontinued
0.6814	Remote Similarity	NPD4111	Phase 1
0.6806	Remote Similarity	NPD7669	Phase 3
0.6804	Remote Similarity	NPD4107	Approved
0.68	Remote Similarity	NPD6844	Discontinued
0.68	Remote Similarity	NPD5676	Approved
0.68	Remote Similarity	NPD228	Approved
0.6798	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6895	Approved
0.6788	Remote Similarity	NPD6896	Approved
0.6786	Remote Similarity	NPD5177	Phase 3
0.678	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1421	Approved
0.6772	Remote Similarity	NPD1420	Approved
0.6768	Remote Similarity	NPD230	Phase 1
0.6766	Remote Similarity	NPD3656	Approved
0.6765	Remote Similarity	NPD3845	Phase 1
0.6761	Remote Similarity	NPD1465	Phase 2
0.6758	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4040	Phase 1
0.674	Remote Similarity	NPD2969	Approved
0.674	Remote Similarity	NPD2970	Approved
0.6725	Remote Similarity	NPD4357	Discontinued
0.6722	Remote Similarity	NPD7802	Discontinued
0.6721	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4580	Approved
0.6705	Remote Similarity	NPD7427	Discontinued
0.6705	Remote Similarity	NPD7248	Discontinued
0.6705	Remote Similarity	NPD1934	Approved
0.6703	Remote Similarity	NPD3823	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