Structure

Physi-Chem Properties

Molecular Weight:  238.16
Volume:  254.685
LogP:  1.608
LogD:  1.322
LogS:  -2.745
# Rotatable Bonds:  1
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.76
Synthetic Accessibility Score:  4.146
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.452
MDCK Permeability:  2.546325049479492e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.023
30% Bioavailability (F30%):  0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.885
Plasma Protein Binding (PPB):  67.70835876464844%
Volume Distribution (VD):  0.922
Pgp-substrate:  28.062698364257812%

ADMET: Metabolism

CYP1A2-inhibitor:  0.027
CYP1A2-substrate:  0.606
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.892
CYP2C9-inhibitor:  0.041
CYP2C9-substrate:  0.484
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.299
CYP3A4-inhibitor:  0.099
CYP3A4-substrate:  0.694

ADMET: Excretion

Clearance (CL):  9.41
Half-life (T1/2):  0.735

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.328
Drug-inuced Liver Injury (DILI):  0.457
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.637
Maximum Recommended Daily Dose:  0.164
Skin Sensitization:  0.038
Carcinogencity:  0.318
Eye Corrosion:  0.03
Eye Irritation:  0.206
Respiratory Toxicity:  0.03

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  Natural Product: NPC110150

Natural Product ID:  NPC110150
Common Name*:   Oxyphyllenodiol A
IUPAC Name:   (4S,5S,6R)-5,6-dihydroxy-6-methyl-4-propan-2-yl-2,3,4,5,7,8-hexahydronaphthalen-1-one
Synonyms:  
Standard InCHIKey:  SZSSWPDHIZIMCT-QCZZGDTMSA-N
Standard InCHI:  InChI=1S/C14H22O3/c1-8(2)9-4-5-11(15)10-6-7-14(3,17)13(16)12(9)10/h8-9,13,16-17H,4-7H2,1-3H3/t9-,13-,14+/m0/s1
SMILES:  CC([C@@H]1CCC(=O)C2=C1[C@H](O)[C@](CC2)(C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL304564
PubChem CID:   10082923
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003487] Cyclic ketones
              • [CHEMONTID:0004325] Cyclohexenones

*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
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(81)85171-0]
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. PMID[10924179]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota Whole plant n.a. n.a. PMID[11141121]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[11514174]
NPO8035 Tylophora tanakae Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12350151]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota fruit Hainan Island, China 1998 PMID[12398545]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota stems Wulai Hsiang, Taipei County, Taiwan 2005-MAY PMID[17253858]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[18057725]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[18293903]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. PMID[19432411]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19581087]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20299229]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota bark n.a. n.a. PMID[20363129]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21214253]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[22277277]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota Leaves n.a. n.a. PMID[23025417]
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. PMID[23131412]
NPO25106 Arnica parryi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[23583435]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. PMID[24669201]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[25757283]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota stem bark Laifeng, Hubei Province, China 2012-JUL PMID[26087384]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota Fruit juice n.a. n.a. PMID[3404148]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[9157192]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota stem bark n.a. n.a. PMID[9157192]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23288 Justicia betonica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23837 Rubus laciniatus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO761 Fagus fusca Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5384 Ligustrum obtusifolium Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25130 Hylotrupes bajulus Species Cerambycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7045 Viviparus japonicus Species Viviparidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12436 Quercus imbricaria Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27093 Kniphofia foliosa Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25106 Arnica parryi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21483 0nomuraea dietziae Species Streptosporangiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24813 Agardhiella tenera Species Solieriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27277 Stenocarpella maydis Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11256 Pseudowintera colorata Species Winteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20291 Phyllanthus oligospermus Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24688 Streptomyces ramocissimus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7709 Spiracantha cornifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8035 Tylophora tanakae Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10737 Asteriscus aquaticus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13455 Hemiselmis virescens Species Hemiselmidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23375 Hypericum reptans Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9672 Lotus ucrainicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24406 Rhizophora tagal Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23657 Ophiocordyceps heteropoda Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24900 Vladimiria muliensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO1182 Croton montevidensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9509 Charpentiera obovata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25226 Kalanchoe spathulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5008 Hubertia tomentosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24493 Echinacea simulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2608 Solanum andigena Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12544 Dioscorea olfersiana Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24268 Pteryxia terebinthina Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18875 Aconitum contortum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24843 Pachygone dasycarpa Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24589 Grindelia discoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24969 Ageratum mexicanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24754 Tsitsikamma favus Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21799 Bacillus litoralis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15252 Clathria prolifera Species Microcionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23547 Strychnos amazonica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24118 Buxus hildebrandtii Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23288 Justicia betonica Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22924 Bombus terrestris Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3378 Alstonia undulifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11553 Phebalium dentatum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8477 Myristica cagayanensis Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23750 Escontria chiotilla Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10393 Ophidiaster ophidianus Species Ophidiasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5823 Helichrysum auriceps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29503 Alstonia spectabilis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24559 Cotinus coggygria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12308 Metridium senile Species Metridiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27031 Methanosarcina barkeri Species Methanosarcinaceae Archaea n.a. n.a. n.a. Database[UNPD]
NPO12888 Echinus microtuberculatus Species Echinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22715 Alpinia oxyphylla Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24021 Eucryphia cordifolia Species Cunoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17445 Streptomyces corchorusii Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24456 Salvia lavandulifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25031 Petunia nyctaginiflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24659 Eremurus chinensis Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4493 Polygonum flaccidum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19716 Uvaria lucida Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23660 Alpinia zerumbet Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9922 Myelobia smerintha Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3736 Scrophularia koelzii Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25068 Zebrina pendula Species Enidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24328 Gratiola officinalis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11811 Capparis ovata Species Capparaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23478 Uncaria africana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23149 Callistemon coccineus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24874 Croton geayi Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12188 Datisca glomerata Species Datiscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21242 Neolitsea villosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6253 Conus pulicarius Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12669 Cassine papillosa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18045 Holothuria atra Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1674 Dalbergia nitidula Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28259 Viguiera pinnatilobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24191 Drypetes tessmanniana Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22375 Saussurea salicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24937 Callicarpa acuminata Species Lamiaceae 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
NPT521 Cell Line RBL-2H3 Rattus norvegicus Inhibition = 1.1 % PMID[484942]
NPT521 Cell Line RBL-2H3 Rattus norvegicus Inhibition = 0.4 % PMID[484942]
NPT521 Cell Line RBL-2H3 Rattus norvegicus Inhibition = 1.7 % PMID[484942]
NPT34 Cell Line BV-2 Mus musculus MNTD = 100.0 uM PMID[484943]
NPT32 Organism Mus musculus Mus musculus Inhibition = 11.8 % PMID[484941]
NPT32 Organism Mus musculus Mus musculus Inhibition < 16.9 % PMID[484941]
NPT32 Organism Mus musculus Mus musculus Inhibition < 52.5 % PMID[484941]
NPT32 Organism Mus musculus Mus musculus Inhibition < 101.7 % PMID[484941]
NPT32 Organism Mus musculus Mus musculus IC50 = 28000.0 nM PMID[484941]
NPT2 Others Unspecified Inhibition = 101.7 % PMID[484942]
NPT2 Others Unspecified Inhibition = 11.8 % PMID[484942]
NPT2 Others Unspecified Inhibition = 16.9 % PMID[484942]
NPT2 Others Unspecified Inhibition = 52.5 % PMID[484942]
NPT2 Others Unspecified IC50 = 28000.0 nM PMID[484942]

☑ 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 NPC110150 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
1.0 High Similarity NPC66764
0.8636 High Similarity NPC196227
0.8621 High Similarity NPC116726
0.8554 High Similarity NPC169941
0.8554 High Similarity NPC251475
0.8452 Intermediate Similarity NPC40687
0.8427 Intermediate Similarity NPC472977
0.8427 Intermediate Similarity NPC472976
0.837 Intermediate Similarity NPC198880
0.8333 Intermediate Similarity NPC64600
0.8295 Intermediate Similarity NPC134321
0.8293 Intermediate Similarity NPC281138
0.8256 Intermediate Similarity NPC472974
0.8202 Intermediate Similarity NPC63748
0.8202 Intermediate Similarity NPC73457
0.8191 Intermediate Similarity NPC473424
0.8182 Intermediate Similarity NPC472973
0.8152 Intermediate Similarity NPC161147
0.8148 Intermediate Similarity NPC472305
0.8132 Intermediate Similarity NPC259286
0.8132 Intermediate Similarity NPC200702
0.8125 Intermediate Similarity NPC470299
0.8111 Intermediate Similarity NPC69454
0.8095 Intermediate Similarity NPC470298
0.8095 Intermediate Similarity NPC119229
0.809 Intermediate Similarity NPC473099
0.809 Intermediate Similarity NPC128672
0.8072 Intermediate Similarity NPC308038
0.8049 Intermediate Similarity NPC34110
0.8043 Intermediate Similarity NPC249954
0.8043 Intermediate Similarity NPC117133
0.8 Intermediate Similarity NPC472978
0.8 Intermediate Similarity NPC93590
0.7978 Intermediate Similarity NPC473100
0.7976 Intermediate Similarity NPC271104
0.7976 Intermediate Similarity NPC472301
0.7976 Intermediate Similarity NPC172013
0.7955 Intermediate Similarity NPC220930
0.7955 Intermediate Similarity NPC272039
0.7938 Intermediate Similarity NPC323834
0.7935 Intermediate Similarity NPC473170
0.7927 Intermediate Similarity NPC7629
0.7927 Intermediate Similarity NPC151622
0.7912 Intermediate Similarity NPC109305
0.7907 Intermediate Similarity NPC105173
0.7889 Intermediate Similarity NPC230332
0.7865 Intermediate Similarity NPC131470
0.7865 Intermediate Similarity NPC143767
0.7865 Intermediate Similarity NPC158778
0.7849 Intermediate Similarity NPC471463
0.7841 Intermediate Similarity NPC472986
0.7841 Intermediate Similarity NPC472985
0.7841 Intermediate Similarity NPC179591
0.7831 Intermediate Similarity NPC257666
0.7831 Intermediate Similarity NPC266193
0.7831 Intermediate Similarity NPC197659
0.7812 Intermediate Similarity NPC477915
0.7805 Intermediate Similarity NPC114236
0.7802 Intermediate Similarity NPC475441
0.7802 Intermediate Similarity NPC99380
0.7802 Intermediate Similarity NPC233116
0.7802 Intermediate Similarity NPC472975
0.7789 Intermediate Similarity NPC316964
0.7778 Intermediate Similarity NPC65941
0.7778 Intermediate Similarity NPC86319
0.7778 Intermediate Similarity NPC275740
0.7778 Intermediate Similarity NPC472983
0.7766 Intermediate Similarity NPC474785
0.7766 Intermediate Similarity NPC474938
0.7765 Intermediate Similarity NPC74445
0.7765 Intermediate Similarity NPC157895
0.7765 Intermediate Similarity NPC104120
0.7765 Intermediate Similarity NPC148685
0.7765 Intermediate Similarity NPC287817
0.7755 Intermediate Similarity NPC149047
0.7753 Intermediate Similarity NPC138756
0.7753 Intermediate Similarity NPC472324
0.7753 Intermediate Similarity NPC471792
0.7742 Intermediate Similarity NPC174948
0.7742 Intermediate Similarity NPC316215
0.7742 Intermediate Similarity NPC318282
0.7742 Intermediate Similarity NPC173875
0.7742 Intermediate Similarity NPC469995
0.7738 Intermediate Similarity NPC80088
0.7738 Intermediate Similarity NPC62336
0.7738 Intermediate Similarity NPC253561
0.7738 Intermediate Similarity NPC475994
0.7738 Intermediate Similarity NPC178852
0.7738 Intermediate Similarity NPC207772
0.7732 Intermediate Similarity NPC473624
0.7727 Intermediate Similarity NPC15807
0.7717 Intermediate Similarity NPC477435
0.7717 Intermediate Similarity NPC477436
0.7717 Intermediate Similarity NPC472930
0.7711 Intermediate Similarity NPC186554
0.7711 Intermediate Similarity NPC239758
0.7711 Intermediate Similarity NPC76966
0.7711 Intermediate Similarity NPC470525
0.7711 Intermediate Similarity NPC263582
0.7708 Intermediate Similarity NPC302537
0.7708 Intermediate Similarity NPC163372
0.7701 Intermediate Similarity NPC297398
0.7692 Intermediate Similarity NPC48010
0.7692 Intermediate Similarity NPC183283
0.7692 Intermediate Similarity NPC136801
0.7677 Intermediate Similarity NPC220229
0.7677 Intermediate Similarity NPC475060
0.7667 Intermediate Similarity NPC328539
0.7667 Intermediate Similarity NPC471722
0.7667 Intermediate Similarity NPC476796
0.766 Intermediate Similarity NPC328371
0.7653 Intermediate Similarity NPC209502
0.7653 Intermediate Similarity NPC204833
0.7647 Intermediate Similarity NPC19900
0.764 Intermediate Similarity NPC72133
0.764 Intermediate Similarity NPC473226
0.764 Intermediate Similarity NPC476043
0.7634 Intermediate Similarity NPC184870
0.7634 Intermediate Similarity NPC166906
0.7634 Intermediate Similarity NPC470958
0.7634 Intermediate Similarity NPC470957
0.7629 Intermediate Similarity NPC308726
0.7629 Intermediate Similarity NPC295791
0.7629 Intermediate Similarity NPC119601
0.7619 Intermediate Similarity NPC74995
0.7614 Intermediate Similarity NPC227132
0.7614 Intermediate Similarity NPC476412
0.7614 Intermediate Similarity NPC470812
0.7609 Intermediate Similarity NPC475806
0.76 Intermediate Similarity NPC217201
0.7586 Intermediate Similarity NPC158411
0.7586 Intermediate Similarity NPC38796
0.7582 Intermediate Similarity NPC123912
0.7582 Intermediate Similarity NPC472489
0.7582 Intermediate Similarity NPC214387
0.7582 Intermediate Similarity NPC77263
0.7582 Intermediate Similarity NPC473999
0.7582 Intermediate Similarity NPC469319
0.7582 Intermediate Similarity NPC309603
0.7582 Intermediate Similarity NPC250592
0.7582 Intermediate Similarity NPC229871
0.7579 Intermediate Similarity NPC18319
0.7579 Intermediate Similarity NPC135685
0.7579 Intermediate Similarity NPC470522
0.7579 Intermediate Similarity NPC320306
0.7576 Intermediate Similarity NPC171137
0.7576 Intermediate Similarity NPC152695
0.7576 Intermediate Similarity NPC202167
0.7576 Intermediate Similarity NPC150531
0.7576 Intermediate Similarity NPC50692
0.7576 Intermediate Similarity NPC48733
0.7576 Intermediate Similarity NPC49958
0.7576 Intermediate Similarity NPC97202
0.7576 Intermediate Similarity NPC214264
0.7576 Intermediate Similarity NPC302607
0.7576 Intermediate Similarity NPC260268
0.7576 Intermediate Similarity NPC296945
0.7576 Intermediate Similarity NPC476027
0.7576 Intermediate Similarity NPC319077
0.7576 Intermediate Similarity NPC85829
0.7561 Intermediate Similarity NPC247586
0.7561 Intermediate Similarity NPC261316
0.7561 Intermediate Similarity NPC265485
0.7561 Intermediate Similarity NPC49737
0.7561 Intermediate Similarity NPC220939
0.7556 Intermediate Similarity NPC241875
0.7556 Intermediate Similarity NPC469317
0.7556 Intermediate Similarity NPC469314
0.7556 Intermediate Similarity NPC99909
0.7553 Intermediate Similarity NPC297199
0.7553 Intermediate Similarity NPC37646
0.7553 Intermediate Similarity NPC476245
0.7553 Intermediate Similarity NPC477437
0.7553 Intermediate Similarity NPC470016
0.7553 Intermediate Similarity NPC271195
0.7553 Intermediate Similarity NPC134067
0.7553 Intermediate Similarity NPC53565
0.7553 Intermediate Similarity NPC477438
0.7553 Intermediate Similarity NPC472932
0.7553 Intermediate Similarity NPC317586
0.7551 Intermediate Similarity NPC251017
0.7551 Intermediate Similarity NPC55872
0.7531 Intermediate Similarity NPC173321
0.7528 Intermediate Similarity NPC79573
0.7528 Intermediate Similarity NPC197823
0.7528 Intermediate Similarity NPC474853
0.7528 Intermediate Similarity NPC476426
0.7528 Intermediate Similarity NPC179006
0.7527 Intermediate Similarity NPC474736
0.7526 Intermediate Similarity NPC472637
0.7526 Intermediate Similarity NPC470184
0.7525 Intermediate Similarity NPC214644
0.7525 Intermediate Similarity NPC11710
0.75 Intermediate Similarity NPC472325
0.75 Intermediate Similarity NPC471783
0.75 Intermediate Similarity NPC477916
0.75 Intermediate Similarity NPC9457
0.75 Intermediate Similarity NPC83744
0.75 Intermediate Similarity NPC10364
0.75 Intermediate Similarity NPC478056

  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 NPC110150 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
0.7582 Intermediate Similarity NPD5328 Approved
0.7444 Intermediate Similarity NPD3618 Phase 1
0.7419 Intermediate Similarity NPD6079 Approved
0.7342 Intermediate Similarity NPD7341 Phase 2
0.7333 Intermediate Similarity NPD1696 Phase 3
0.7273 Intermediate Similarity NPD5211 Phase 2
0.7216 Intermediate Similarity NPD4755 Approved
0.7191 Intermediate Similarity NPD3667 Approved
0.7158 Intermediate Similarity NPD4202 Approved
0.7129 Intermediate Similarity NPD5141 Approved
0.7113 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD5221 Approved
0.7113 Intermediate Similarity NPD5222 Approved
0.7113 Intermediate Similarity NPD4697 Phase 3
0.7071 Intermediate Similarity NPD5286 Approved
0.7071 Intermediate Similarity NPD4696 Approved
0.7071 Intermediate Similarity NPD4700 Approved
0.7071 Intermediate Similarity NPD5285 Approved
0.7053 Intermediate Similarity NPD7515 Phase 2
0.7041 Intermediate Similarity NPD5173 Approved
0.7033 Intermediate Similarity NPD3666 Approved
0.7033 Intermediate Similarity NPD3665 Phase 1
0.7033 Intermediate Similarity NPD3133 Approved
0.7033 Intermediate Similarity NPD4786 Approved
0.7 Intermediate Similarity NPD5223 Approved
0.6979 Remote Similarity NPD5779 Approved
0.6979 Remote Similarity NPD5778 Approved
0.6931 Remote Similarity NPD5226 Approved
0.6931 Remote Similarity NPD4633 Approved
0.6931 Remote Similarity NPD5224 Approved
0.6931 Remote Similarity NPD5225 Approved
0.6882 Remote Similarity NPD5279 Phase 3
0.6882 Remote Similarity NPD4519 Discontinued
0.6882 Remote Similarity NPD4623 Approved
0.6863 Remote Similarity NPD5175 Approved
0.6863 Remote Similarity NPD5174 Approved
0.6863 Remote Similarity NPD4754 Approved
0.6829 Remote Similarity NPD7331 Phase 2
0.6792 Remote Similarity NPD4634 Approved
0.6742 Remote Similarity NPD3617 Approved
0.6735 Remote Similarity NPD7748 Approved
0.6731 Remote Similarity NPD4768 Approved
0.6731 Remote Similarity NPD6402 Approved
0.6731 Remote Similarity NPD7128 Approved
0.6731 Remote Similarity NPD5739 Approved
0.6731 Remote Similarity NPD4767 Approved
0.6731 Remote Similarity NPD6675 Approved
0.6727 Remote Similarity NPD7115 Discovery
0.6702 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6698 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4753 Phase 2
0.6667 Remote Similarity NPD5697 Approved
0.6667 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD6101 Approved
0.6634 Remote Similarity NPD4225 Approved
0.6632 Remote Similarity NPD3573 Approved
0.663 Remote Similarity NPD4221 Approved
0.663 Remote Similarity NPD4223 Phase 3
0.663 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6606 Remote Similarity NPD4632 Approved
0.6604 Remote Similarity NPD4729 Approved
0.6604 Remote Similarity NPD6011 Approved
0.6604 Remote Similarity NPD7320 Approved
0.6604 Remote Similarity NPD6899 Approved
0.6604 Remote Similarity NPD6881 Approved
0.6604 Remote Similarity NPD4730 Approved
0.6604 Remote Similarity NPD5128 Approved
0.6596 Remote Similarity NPD1694 Approved
0.6593 Remote Similarity NPD4695 Discontinued
0.6593 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6591 Remote Similarity NPD8264 Approved
0.6543 Remote Similarity NPD368 Approved
0.6542 Remote Similarity NPD6012 Approved
0.6542 Remote Similarity NPD6373 Approved
0.6542 Remote Similarity NPD6013 Approved
0.6542 Remote Similarity NPD6372 Approved
0.6542 Remote Similarity NPD6014 Approved
0.6535 Remote Similarity NPD7902 Approved
0.6531 Remote Similarity NPD6411 Approved
0.6526 Remote Similarity NPD5690 Phase 2
0.6526 Remote Similarity NPD4694 Approved
0.6526 Remote Similarity NPD5280 Approved
0.6522 Remote Similarity NPD4692 Approved
0.6522 Remote Similarity NPD4139 Approved
0.6514 Remote Similarity NPD8297 Approved
0.6489 Remote Similarity NPD4197 Approved
0.6489 Remote Similarity NPD3668 Phase 3
0.6481 Remote Similarity NPD6883 Approved
0.6481 Remote Similarity NPD5169 Approved
0.6481 Remote Similarity NPD5250 Approved
0.6481 Remote Similarity NPD7102 Approved
0.6481 Remote Similarity NPD5248 Approved
0.6481 Remote Similarity NPD7290 Approved
0.6481 Remote Similarity NPD5135 Approved
0.6481 Remote Similarity NPD5249 Phase 3
0.6481 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6481 Remote Similarity NPD5251 Approved
0.6481 Remote Similarity NPD5247 Approved
0.6449 Remote Similarity NPD5168 Approved
0.6422 Remote Similarity NPD5127 Approved
0.6422 Remote Similarity NPD6650 Approved
0.6422 Remote Similarity NPD5215 Approved
0.6422 Remote Similarity NPD5216 Approved
0.6422 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6422 Remote Similarity NPD8130 Phase 1
0.6422 Remote Similarity NPD5217 Approved
0.6422 Remote Similarity NPD6649 Approved
0.6422 Remote Similarity NPD6869 Approved
0.6422 Remote Similarity NPD6617 Approved
0.6422 Remote Similarity NPD6847 Approved
0.6421 Remote Similarity NPD5329 Approved
0.6413 Remote Similarity NPD4748 Discontinued
0.6408 Remote Similarity NPD7640 Approved
0.6408 Remote Similarity NPD7639 Approved
0.6404 Remote Similarity NPD3703 Phase 2
0.6364 Remote Similarity NPD6882 Approved
0.6354 Remote Similarity NPD4138 Approved
0.6354 Remote Similarity NPD4688 Approved
0.6354 Remote Similarity NPD5205 Approved
0.6354 Remote Similarity NPD4689 Approved
0.6354 Remote Similarity NPD4693 Phase 3
0.6354 Remote Similarity NPD4690 Approved
0.6337 Remote Similarity NPD5695 Phase 3
0.6337 Remote Similarity NPD5210 Approved
0.6337 Remote Similarity NPD4629 Approved
0.633 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6327 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7638 Approved
0.63 Remote Similarity NPD6399 Phase 3
0.6286 Remote Similarity NPD7632 Discontinued
0.6283 Remote Similarity NPD6009 Approved
0.6262 Remote Similarity NPD6008 Approved
0.6261 Remote Similarity NPD6319 Approved
0.625 Remote Similarity NPD7520 Clinical (unspecified phase)
0.625 Remote Similarity NPD5167 Approved
0.625 Remote Similarity NPD5363 Approved
0.6239 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6238 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6238 Remote Similarity NPD7900 Approved
0.6235 Remote Similarity NPD3704 Approved
0.6224 Remote Similarity NPD4518 Approved
0.6216 Remote Similarity NPD6053 Discontinued
0.6214 Remote Similarity NPD6083 Phase 2
0.6214 Remote Similarity NPD6084 Phase 2
0.6211 Remote Similarity NPD4788 Approved
0.6211 Remote Similarity NPD6110 Phase 1
0.6207 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6207 Remote Similarity NPD3699 Clinical (unspecified phase)
0.62 Remote Similarity NPD5281 Approved
0.62 Remote Similarity NPD5284 Approved
0.6195 Remote Similarity NPD6274 Approved
0.6186 Remote Similarity NPD7334 Approved
0.6186 Remote Similarity NPD7146 Approved
0.6186 Remote Similarity NPD5786 Approved
0.6186 Remote Similarity NPD6409 Approved
0.6186 Remote Similarity NPD5330 Approved
0.6186 Remote Similarity NPD6684 Approved
0.6186 Remote Similarity NPD7521 Approved
0.6154 Remote Similarity NPD3701 Clinical (unspecified phase)
0.614 Remote Similarity NPD6317 Approved
0.6139 Remote Similarity NPD5133 Approved
0.6129 Remote Similarity NPD7645 Phase 2
0.6122 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6121 Remote Similarity NPD6054 Approved
0.6121 Remote Similarity NPD6059 Approved
0.6105 Remote Similarity NPD4269 Approved
0.6105 Remote Similarity NPD4270 Approved
0.61 Remote Similarity NPD6698 Approved
0.61 Remote Similarity NPD4096 Approved
0.61 Remote Similarity NPD46 Approved
0.6087 Remote Similarity NPD6313 Approved
0.6087 Remote Similarity NPD6335 Approved
0.6087 Remote Similarity NPD6314 Approved
0.6068 Remote Similarity NPD6016 Approved
0.6068 Remote Similarity NPD5983 Phase 2
0.6068 Remote Similarity NPD6015 Approved
0.6067 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6067 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6064 Remote Similarity NPD7525 Registered
0.6061 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6061 Remote Similarity NPD6903 Approved
0.6055 Remote Similarity NPD6412 Phase 2
0.6055 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6053 Remote Similarity NPD6868 Approved
0.6044 Remote Similarity NPD6942 Approved
0.6044 Remote Similarity NPD7339 Approved
0.6042 Remote Similarity NPD5362 Discontinued
0.604 Remote Similarity NPD7983 Approved
0.6038 Remote Similarity NPD5344 Discontinued
0.6034 Remote Similarity NPD7100 Approved
0.6034 Remote Similarity NPD7101 Approved
0.6022 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6019 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6017 Remote Similarity NPD5988 Approved
0.6017 Remote Similarity NPD6370 Approved
0.6 Remote Similarity NPD342 Phase 1
0.6 Remote Similarity NPD5696 Approved
0.6 Remote Similarity NPD7507 Approved
0.6 Remote Similarity NPD8295 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