Structure

Physi-Chem Properties

Molecular Weight:  148.05
Volume:  154.142
LogP:  2.04
LogD:  1.844
LogS:  -2.787
# Rotatable Bonds:  0
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.412
Synthetic Accessibility Score:  2.091
Fsp3:  0.222
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.501
MDCK Permeability:  3.027497950824909e-05
Pgp-inhibitor:  0.023
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.146

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.868
Plasma Protein Binding (PPB):  77.26774597167969%
Volume Distribution (VD):  0.465
Pgp-substrate:  21.994062423706055%

ADMET: Metabolism

CYP1A2-inhibitor:  0.964
CYP1A2-substrate:  0.147
CYP2C19-inhibitor:  0.713
CYP2C19-substrate:  0.167
CYP2C9-inhibitor:  0.152
CYP2C9-substrate:  0.743
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.762
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.24

ADMET: Excretion

Clearance (CL):  10.207
Half-life (T1/2):  0.83

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.021
Drug-inuced Liver Injury (DILI):  0.047
AMES Toxicity:  0.069
Rat Oral Acute Toxicity:  0.045
Maximum Recommended Daily Dose:  0.079
Skin Sensitization:  0.943
Carcinogencity:  0.796
Eye Corrosion:  0.931
Eye Irritation:  0.979
Respiratory Toxicity:  0.373

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  Natural Product: NPC233238

Natural Product ID:  NPC233238
Common Name*:   Dihydrocoumarin
IUPAC Name:   3,4-dihydrochromen-2-one
Synonyms:   Chroman-2-One; Dihydrocoumarin
Standard InCHIKey:  VMUXSMXIQBNMGZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2
SMILES:  O=C1CCc2c(O1)cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL89306
PubChem CID:   660
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002642] 3,4-dihydrocoumarins

*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
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10843584]
NPO27252 Iochroma australe Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12027740]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. antarctic n.a. PMID[15270575]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[15497934]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. fruit n.a. PMID[16378372]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. flower n.a. PMID[16378372]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[30407007]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27109 Uncaria roxburghiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27109 Uncaria roxburghiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30570 Tetrapanax papyriferus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26352 Heuchera cylindrica Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26678 Calea pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26408 Melanophryniscus moreirae Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26535 Balanus glandula Species Balanidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11845 Petrorhagia dubia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3346 Piper sanctum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18292 Guarea trichilioides Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25849 Streptomyces lomondensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29051 Ranunculus acris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26289 Lecidella chodati Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13991 Iris cristata Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25793 Gremmeniella abietina Species Helotiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26453 Prunus lusitanica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26952 Cineraria geifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26053 Pluchea suaveolens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26377 Amelanchier vulgaris Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26563 Alectoria japonica Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25821 Delphinium cashmerianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27377 Diaporthe helianthi Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26186 Stereocaulon leprocauloides Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26026 Vitis silvestris Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26884 Helichrysum davenportii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13781 Eremostachys moluccelloides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25741 Aster ageratoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25976 Dendronephthya gigantea Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25717 Maytenus hookeri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26430 Aplysina laevis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7214 Bufotes viridis Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26754 Stevia connata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26163 Anisodus tanguticus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27252 Iochroma australe Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26782 Dendrilla membranosa Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2039 Callerya cinerea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26244 Panax papyrifer Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26078 Mussaenda parviflora Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2344 Carlina acanthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26903 Plectranthus purpuratus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27109 Uncaria roxburghiana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO137 Nepeta multifida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26135 Walsura tubulata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26213 Tephrosia vogelii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14810 Araucaria imbricata Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25997 Senecio rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14466 Penicillium olsonii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26980 Halocarpus biformis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2720 Dactylorhiza hatagirea Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19823 Vicia benghalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25952 Lastrea thelypteris n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26109 Pilocarpus spicatus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8806 Artemisia marschalliana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25926 Tephrosia pumila Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25873 Thaminophyllum multiflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24378 Osmanthus heterophyllus Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12524 Teucridium parvifolium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26727 Eremocarpus setiger n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO19849 Melilotus officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26625 Stichopus chloronotus Species Stichopodidae 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT4620 Individual Protein NAD-dependent histone deacetylase SIR2 Saccharomyces cerevisiae S288c MGC = 0.85 uM PMID[463783]
NPT4620 Individual Protein NAD-dependent histone deacetylase SIR2 Saccharomyces cerevisiae S288c IC50 = 122000.0 nM PMID[463783]
NPT4620 Individual Protein NAD-dependent histone deacetylase SIR2 Saccharomyces cerevisiae S288c SI = 144.0 n.a. PMID[463783]
NPT4620 Individual Protein NAD-dependent histone deacetylase SIR2 Saccharomyces cerevisiae S288c Inhibition = 0.15 uM PMID[463783]
NPT1652 Individual Protein Serum paraoxonase/arylesterase 1 Homo sapiens Activity = 12.99 umol/min/mg PMID[463784]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PMID[463785]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 8912.5 nM PMID[463785]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 53088.44 nM PMID[463786]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[463786]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 74978.0 nM PMID[463787]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 5623.4 nM PMID[463785]
NPT2 Others Unspecified Potency n.a. 2199.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 695.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 77350.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 195 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61441.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61652.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 39114.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54759.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68938.5 nM PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC233238 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9065 High Similarity NPC259554
0.8803 High Similarity NPC107846
0.8696 High Similarity NPC474874
0.8692 High Similarity NPC139891
0.8673 High Similarity NPC470860
0.8611 High Similarity NPC1065
0.8585 High Similarity NPC307425
0.8584 High Similarity NPC51345
0.8545 High Similarity NPC149545
0.8491 Intermediate Similarity NPC107101
0.8448 Intermediate Similarity NPC264976
0.8378 Intermediate Similarity NPC234639
0.8376 Intermediate Similarity NPC230951
0.8349 Intermediate Similarity NPC473855
0.8348 Intermediate Similarity NPC33717
0.8333 Intermediate Similarity NPC298224
0.8333 Intermediate Similarity NPC89630
0.8319 Intermediate Similarity NPC280760
0.8304 Intermediate Similarity NPC141068
0.8291 Intermediate Similarity NPC35744
0.8276 Intermediate Similarity NPC45104
0.8264 Intermediate Similarity NPC88403
0.8264 Intermediate Similarity NPC165556
0.8261 Intermediate Similarity NPC322358
0.8257 Intermediate Similarity NPC283546
0.8257 Intermediate Similarity NPC38209
0.8226 Intermediate Similarity NPC109778
0.8205 Intermediate Similarity NPC152159
0.8205 Intermediate Similarity NPC293424
0.8205 Intermediate Similarity NPC32298
0.8182 Intermediate Similarity NPC473393
0.8174 Intermediate Similarity NPC87563
0.8167 Intermediate Similarity NPC311219
0.8158 Intermediate Similarity NPC266116
0.8142 Intermediate Similarity NPC88868
0.8142 Intermediate Similarity NPC231251
0.8142 Intermediate Similarity NPC25067
0.8136 Intermediate Similarity NPC54243
0.8131 Intermediate Similarity NPC95755
0.813 Intermediate Similarity NPC37512
0.813 Intermediate Similarity NPC161322
0.8125 Intermediate Similarity NPC291837
0.812 Intermediate Similarity NPC217423
0.8103 Intermediate Similarity NPC188907
0.8103 Intermediate Similarity NPC220540
0.8095 Intermediate Similarity NPC269421
0.8087 Intermediate Similarity NPC109241
0.8083 Intermediate Similarity NPC314329
0.808 Intermediate Similarity NPC2989
0.807 Intermediate Similarity NPC23332
0.8067 Intermediate Similarity NPC193193
0.8067 Intermediate Similarity NPC31314
0.8065 Intermediate Similarity NPC2401
0.8051 Intermediate Similarity NPC96705
0.8049 Intermediate Similarity NPC237868
0.8034 Intermediate Similarity NPC128633
0.8033 Intermediate Similarity NPC229113
0.8018 Intermediate Similarity NPC227255
0.8018 Intermediate Similarity NPC238115
0.8018 Intermediate Similarity NPC475269
0.8018 Intermediate Similarity NPC128730
0.8017 Intermediate Similarity NPC252004
0.8017 Intermediate Similarity NPC291189
0.8017 Intermediate Similarity NPC69403
0.8 Intermediate Similarity NPC473019
0.8 Intermediate Similarity NPC170546
0.8 Intermediate Similarity NPC66246
0.7983 Intermediate Similarity NPC98748
0.7982 Intermediate Similarity NPC183648
0.7969 Intermediate Similarity NPC34456
0.7951 Intermediate Similarity NPC11799
0.7951 Intermediate Similarity NPC141252
0.7946 Intermediate Similarity NPC326801
0.7946 Intermediate Similarity NPC176971
0.7937 Intermediate Similarity NPC183348
0.7937 Intermediate Similarity NPC473271
0.7937 Intermediate Similarity NPC282230
0.7937 Intermediate Similarity NPC327457
0.7937 Intermediate Similarity NPC86774
0.7931 Intermediate Similarity NPC279916
0.7931 Intermediate Similarity NPC303522
0.7928 Intermediate Similarity NPC109637
0.7917 Intermediate Similarity NPC246214
0.7917 Intermediate Similarity NPC168050
0.7899 Intermediate Similarity NPC152306
0.7899 Intermediate Similarity NPC265547
0.7891 Intermediate Similarity NPC287533
0.7886 Intermediate Similarity NPC221798
0.7881 Intermediate Similarity NPC163398
0.7876 Intermediate Similarity NPC151530
0.7876 Intermediate Similarity NPC157473
0.7874 Intermediate Similarity NPC196979
0.7874 Intermediate Similarity NPC470977
0.7874 Intermediate Similarity NPC470976
0.7874 Intermediate Similarity NPC15083
0.7863 Intermediate Similarity NPC235250
0.7857 Intermediate Similarity NPC238309
0.7851 Intermediate Similarity NPC322569
0.7838 Intermediate Similarity NPC179686
0.7838 Intermediate Similarity NPC13426
0.7833 Intermediate Similarity NPC61779
0.7833 Intermediate Similarity NPC281356
0.7833 Intermediate Similarity NPC234956
0.7833 Intermediate Similarity NPC43435
0.7833 Intermediate Similarity NPC298796
0.7826 Intermediate Similarity NPC473809
0.7823 Intermediate Similarity NPC470858
0.7823 Intermediate Similarity NPC224657
0.7815 Intermediate Similarity NPC183154
0.7815 Intermediate Similarity NPC469954
0.7815 Intermediate Similarity NPC263754
0.7812 Intermediate Similarity NPC175159
0.7812 Intermediate Similarity NPC307289
0.7805 Intermediate Similarity NPC93730
0.7805 Intermediate Similarity NPC472888
0.7795 Intermediate Similarity NPC475102
0.7787 Intermediate Similarity NPC52247
0.7778 Intermediate Similarity NPC53953
0.7769 Intermediate Similarity NPC470092
0.7769 Intermediate Similarity NPC229128
0.7769 Intermediate Similarity NPC14177
0.7769 Intermediate Similarity NPC61499
0.776 Intermediate Similarity NPC475236
0.7759 Intermediate Similarity NPC245552
0.7759 Intermediate Similarity NPC57879
0.7752 Intermediate Similarity NPC55147
0.775 Intermediate Similarity NPC205502
0.775 Intermediate Similarity NPC206007
0.7748 Intermediate Similarity NPC84325
0.7744 Intermediate Similarity NPC254994
0.7742 Intermediate Similarity NPC111347
0.7742 Intermediate Similarity NPC474237
0.7742 Intermediate Similarity NPC193805
0.7734 Intermediate Similarity NPC472517
0.7731 Intermediate Similarity NPC316062
0.7727 Intermediate Similarity NPC253616
0.7727 Intermediate Similarity NPC245561
0.7727 Intermediate Similarity NPC103001
0.7724 Intermediate Similarity NPC473464
0.7724 Intermediate Similarity NPC96286
0.7724 Intermediate Similarity NPC151237
0.7724 Intermediate Similarity NPC248429
0.7724 Intermediate Similarity NPC27198
0.7724 Intermediate Similarity NPC476332
0.7712 Intermediate Similarity NPC114144
0.771 Intermediate Similarity NPC104796
0.7705 Intermediate Similarity NPC180006
0.7705 Intermediate Similarity NPC235190
0.7705 Intermediate Similarity NPC163200
0.7698 Intermediate Similarity NPC49852
0.7698 Intermediate Similarity NPC475496
0.7698 Intermediate Similarity NPC293387
0.7692 Intermediate Similarity NPC199462
0.7686 Intermediate Similarity NPC201284
0.768 Intermediate Similarity NPC2771
0.768 Intermediate Similarity NPC4164
0.768 Intermediate Similarity NPC170749
0.7669 Intermediate Similarity NPC36414
0.7669 Intermediate Similarity NPC473988
0.7667 Intermediate Similarity NPC471498
0.7667 Intermediate Similarity NPC240664
0.7667 Intermediate Similarity NPC471503
0.7664 Intermediate Similarity NPC321956
0.7661 Intermediate Similarity NPC472518
0.7661 Intermediate Similarity NPC315807
0.7658 Intermediate Similarity NPC52472
0.7652 Intermediate Similarity NPC268081
0.7642 Intermediate Similarity NPC187868
0.7638 Intermediate Similarity NPC473907
0.7638 Intermediate Similarity NPC2596
0.7634 Intermediate Similarity NPC298900
0.7634 Intermediate Similarity NPC475011
0.7634 Intermediate Similarity NPC476018
0.7634 Intermediate Similarity NPC470844
0.7634 Intermediate Similarity NPC66705
0.7634 Intermediate Similarity NPC475029
0.7632 Intermediate Similarity NPC326447
0.7632 Intermediate Similarity NPC317592
0.7627 Intermediate Similarity NPC90903
0.7623 Intermediate Similarity NPC247553
0.7619 Intermediate Similarity NPC474476
0.7619 Intermediate Similarity NPC128321
0.7615 Intermediate Similarity NPC66158
0.7615 Intermediate Similarity NPC54503
0.7612 Intermediate Similarity NPC136095
0.7611 Intermediate Similarity NPC114594
0.7611 Intermediate Similarity NPC38079
0.7611 Intermediate Similarity NPC108875
0.7611 Intermediate Similarity NPC2518
0.7603 Intermediate Similarity NPC171023
0.7603 Intermediate Similarity NPC159916
0.76 Intermediate Similarity NPC201667
0.76 Intermediate Similarity NPC470163
0.76 Intermediate Similarity NPC73413
0.76 Intermediate Similarity NPC470162
0.7583 Intermediate Similarity NPC19290
0.7581 Intermediate Similarity NPC257188
0.7581 Intermediate Similarity NPC13007
0.7581 Intermediate Similarity NPC46634
0.7578 Intermediate Similarity NPC474289

  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 NPC233238 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8692 High Similarity NPD9697 Approved
0.8534 High Similarity NPD17 Approved
0.8417 Intermediate Similarity NPD3267 Approved
0.8417 Intermediate Similarity NPD3266 Approved
0.8319 Intermediate Similarity NPD1608 Approved
0.8264 Intermediate Similarity NPD2797 Approved
0.8246 Intermediate Similarity NPD1241 Discontinued
0.8205 Intermediate Similarity NPD1894 Discontinued
0.8167 Intermediate Similarity NPD9717 Approved
0.8158 Intermediate Similarity NPD5535 Approved
0.8115 Intermediate Similarity NPD1203 Approved
0.8083 Intermediate Similarity NPD1535 Discovery
0.8083 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.808 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.808 Intermediate Similarity NPD3268 Approved
0.8067 Intermediate Similarity NPD1778 Approved
0.8065 Intermediate Similarity NPD6832 Phase 2
0.8033 Intermediate Similarity NPD3225 Approved
0.8017 Intermediate Similarity NPD1481 Phase 2
0.7937 Intermediate Similarity NPD1296 Phase 2
0.7903 Intermediate Similarity NPD1019 Discontinued
0.7833 Intermediate Similarity NPD5585 Approved
0.7812 Intermediate Similarity NPD4307 Phase 2
0.7795 Intermediate Similarity NPD6798 Discontinued
0.7787 Intermediate Similarity NPD422 Phase 1
0.7787 Intermediate Similarity NPD1611 Approved
0.7778 Intermediate Similarity NPD2614 Approved
0.7752 Intermediate Similarity NPD4618 Approved
0.7752 Intermediate Similarity NPD4622 Approved
0.7656 Intermediate Similarity NPD2313 Discontinued
0.7642 Intermediate Similarity NPD1281 Approved
0.7634 Intermediate Similarity NPD5689 Approved
0.7634 Intermediate Similarity NPD5688 Approved
0.7632 Intermediate Similarity NPD3134 Approved
0.7615 Intermediate Similarity NPD1933 Approved
0.7615 Intermediate Similarity NPD1184 Approved
0.7615 Intermediate Similarity NPD6355 Discontinued
0.7615 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD8032 Phase 2
0.7576 Intermediate Similarity NPD4308 Phase 3
0.7576 Intermediate Similarity NPD7033 Discontinued
0.7565 Intermediate Similarity NPD1358 Approved
0.7565 Intermediate Similarity NPD290 Approved
0.7561 Intermediate Similarity NPD3496 Discontinued
0.7559 Intermediate Similarity NPD454 Approved
0.752 Intermediate Similarity NPD4359 Approved
0.7519 Intermediate Similarity NPD411 Approved
0.75 Intermediate Similarity NPD6671 Approved
0.75 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD1243 Approved
0.7481 Intermediate Similarity NPD447 Suspended
0.7481 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7478 Intermediate Similarity NPD968 Approved
0.7462 Intermediate Similarity NPD4062 Phase 3
0.7462 Intermediate Similarity NPD6233 Phase 2
0.746 Intermediate Similarity NPD1283 Approved
0.7459 Intermediate Similarity NPD9545 Approved
0.7444 Intermediate Similarity NPD2799 Discontinued
0.7444 Intermediate Similarity NPD3748 Approved
0.744 Intermediate Similarity NPD3972 Approved
0.7438 Intermediate Similarity NPD9493 Approved
0.7419 Intermediate Similarity NPD3847 Discontinued
0.7407 Intermediate Similarity NPD2897 Discontinued
0.7405 Intermediate Similarity NPD3140 Approved
0.7405 Intermediate Similarity NPD3142 Approved
0.7398 Intermediate Similarity NPD1651 Approved
0.7398 Intermediate Similarity NPD5691 Approved
0.7388 Intermediate Similarity NPD4476 Approved
0.7388 Intermediate Similarity NPD4477 Approved
0.7368 Intermediate Similarity NPD9261 Approved
0.735 Intermediate Similarity NPD2684 Approved
0.7344 Intermediate Similarity NPD2798 Approved
0.7338 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2353 Approved
0.7333 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2346 Discontinued
0.7333 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD196 Phase 1
0.7319 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD1549 Phase 2
0.7266 Intermediate Similarity NPD6799 Approved
0.7259 Intermediate Similarity NPD6100 Approved
0.7259 Intermediate Similarity NPD6099 Approved
0.7259 Intermediate Similarity NPD1551 Phase 2
0.7259 Intermediate Similarity NPD2796 Approved
0.7257 Intermediate Similarity NPD1238 Approved
0.7239 Intermediate Similarity NPD1536 Approved
0.7236 Intermediate Similarity NPD7644 Approved
0.7214 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD2557 Approved
0.7209 Intermediate Similarity NPD5647 Approved
0.7206 Intermediate Similarity NPD2344 Approved
0.7206 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4626 Approved
0.7197 Intermediate Similarity NPD4870 Approved
0.7177 Intermediate Similarity NPD1548 Phase 1
0.7176 Intermediate Similarity NPD7095 Approved
0.7174 Intermediate Similarity NPD4628 Phase 3
0.7174 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD3750 Approved
0.7154 Intermediate Similarity NPD2237 Approved
0.7153 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2979 Phase 3
0.7143 Intermediate Similarity NPD1240 Approved
0.7132 Intermediate Similarity NPD6362 Approved
0.7132 Intermediate Similarity NPD1501 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD1537 Approved
0.7132 Intermediate Similarity NPD987 Approved
0.7132 Intermediate Similarity NPD1538 Phase 1
0.7132 Intermediate Similarity NPD1519 Approved
0.7122 Intermediate Similarity NPD2354 Approved
0.7122 Intermediate Similarity NPD3887 Approved
0.7119 Intermediate Similarity NPD9264 Approved
0.7119 Intermediate Similarity NPD9263 Approved
0.7119 Intermediate Similarity NPD9267 Approved
0.7119 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD920 Approved
0.7111 Intermediate Similarity NPD1521 Approved
0.7111 Intermediate Similarity NPD1520 Approved
0.7111 Intermediate Similarity NPD7097 Phase 1
0.7107 Intermediate Similarity NPD7843 Approved
0.7107 Intermediate Similarity NPD821 Approved
0.7087 Intermediate Similarity NPD1091 Approved
0.7087 Intermediate Similarity NPD1610 Phase 2
0.708 Intermediate Similarity NPD6800 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD6002 Phase 3
0.708 Intermediate Similarity NPD6005 Phase 3
0.708 Intermediate Similarity NPD6004 Phase 3
0.708 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD709 Approved
0.7071 Intermediate Similarity NPD6652 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD74 Approved
0.7059 Intermediate Similarity NPD9266 Approved
0.7054 Intermediate Similarity NPD1876 Approved
0.7045 Intermediate Similarity NPD5163 Phase 2
0.7045 Intermediate Similarity NPD2598 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD2486 Discontinued
0.7037 Intermediate Similarity NPD1607 Approved
0.7034 Intermediate Similarity NPD7411 Suspended
0.7029 Intermediate Similarity NPD5958 Discontinued
0.7029 Intermediate Similarity NPD4534 Discontinued
0.7029 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD1137 Approved
0.7025 Intermediate Similarity NPD1139 Approved
0.7015 Intermediate Similarity NPD4060 Phase 1
0.7014 Intermediate Similarity NPD3226 Approved
0.7007 Intermediate Similarity NPD6032 Approved
0.7007 Intermediate Similarity NPD2240 Approved
0.7007 Intermediate Similarity NPD1523 Approved
0.7007 Intermediate Similarity NPD2935 Discontinued
0.7007 Intermediate Similarity NPD1522 Approved
0.7007 Intermediate Similarity NPD2239 Approved
0.7 Intermediate Similarity NPD5451 Approved
0.7 Intermediate Similarity NPD2309 Approved
0.6993 Remote Similarity NPD7427 Discontinued
0.6984 Remote Similarity NPD3443 Approved
0.6984 Remote Similarity NPD3445 Approved
0.6984 Remote Similarity NPD3444 Approved
0.6984 Remote Similarity NPD3049 Approved
0.6978 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6972 Remote Similarity NPD5401 Approved
0.6967 Remote Similarity NPD1138 Approved
0.6966 Remote Similarity NPD6599 Discontinued
0.696 Remote Similarity NPD1758 Phase 1
0.6957 Remote Similarity NPD1471 Phase 3
0.6939 Remote Similarity NPD7819 Suspended
0.6939 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6937 Remote Similarity NPD9365 Approved
0.6935 Remote Similarity NPD6387 Discontinued
0.6935 Remote Similarity NPD7157 Approved
0.6934 Remote Similarity NPD1510 Phase 2
0.6929 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6929 Remote Similarity NPD2556 Approved
0.6929 Remote Similarity NPD4110 Phase 3
0.6929 Remote Similarity NPD2554 Approved
0.6923 Remote Similarity NPD9490 Approved
0.6913 Remote Similarity NPD3749 Approved
0.6912 Remote Similarity NPD6653 Approved
0.6911 Remote Similarity NPD592 Approved
0.6911 Remote Similarity NPD594 Approved
0.6905 Remote Similarity NPD1759 Phase 1
0.6901 Remote Similarity NPD1511 Approved
0.6897 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6889 Remote Similarity NPD4140 Approved
0.6884 Remote Similarity NPD2438 Suspended
0.6884 Remote Similarity NPD2531 Phase 2
0.688 Remote Similarity NPD3596 Phase 2
0.6875 Remote Similarity NPD5403 Approved
0.6875 Remote Similarity NPD3294 Phase 2
0.6866 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6866 Remote Similarity NPD1048 Approved
0.6866 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6864 Remote Similarity NPD164 Approved
0.6864 Remote Similarity NPD5909 Discontinued
0.6857 Remote Similarity NPD1652 Phase 2
0.6855 Remote Similarity NPD690 Clinical (unspecified phase)
0.6853 Remote Similarity NPD3688 Clinical (unspecified phase)

  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