Structure

Physi-Chem Properties

Molecular Weight:  378.24
Volume:  399.441
LogP:  2.524
LogD:  2.76
LogS:  -3.013
# Rotatable Bonds:  3
TPSA:  75.99
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.571
Synthetic Accessibility Score:  6.162
Fsp3:  0.773
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:  -4.758
MDCK Permeability:  5.7429653679719195e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.954
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.159
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.061
Plasma Protein Binding (PPB):  57.0242919921875%
Volume Distribution (VD):  1.355
Pgp-substrate:  44.92066192626953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.076
CYP2C19-inhibitor:  0.011
CYP2C19-substrate:  0.726
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.042
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.081
CYP3A4-inhibitor:  0.135
CYP3A4-substrate:  0.389

ADMET: Excretion

Clearance (CL):  6.533
Half-life (T1/2):  0.514

ADMET: Toxicity

hERG Blockers:  0.489
Human Hepatotoxicity (H-HT):  0.935
Drug-inuced Liver Injury (DILI):  0.62
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.78
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.064
Carcinogencity:  0.144
Eye Corrosion:  0.011
Eye Irritation:  0.028
Respiratory Toxicity:  0.964

Download Data

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

  Natural Product: NPC59570

Natural Product ID:  NPC59570
Common Name*:   5-Methyl-2-Propan-2-Ylcyclohexan-1-One
IUPAC Name:   5-methyl-2-propan-2-ylcyclohexan-1-one
Synonyms:  
Standard InCHIKey:  NFLGAXVYCFJBMK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3
SMILES:  CC(C)C1CCC(C)CC1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1719455
PubChem CID:   6986
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001401] Menthane monoterpenoids

*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
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/hlca.19270100148]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. DOI[10.1078/0176-1617-00195]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[10364842]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[10757735]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[12088434]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[12392098]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[12828478]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota Roots n.a. n.a. PMID[14510592]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[14735439]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Petals n.a. n.a. PMID[15043425]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. root n.a. PMID[15520511]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[15620254]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. callus n.a. PMID[15715262]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[16755060]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. seed n.a. PMID[17345316]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[17666848]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17996677]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[18220354]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[18239311]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19715321]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19785430]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19931461]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19962306]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20078074]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[20121210]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21707257]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[22703163]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[24328283]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24338885]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[24704554]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24996657]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota whole plants Nanning District, Guangxi Province, China 2012-Sep PMID[25647077]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[25767328]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota aerial parts Seoul, Korea n.a. PMID[26331882]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[28445039]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[28558206]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota Roots n.a. n.a. PMID[30024167]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31181920]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31418264]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[32031796]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[32935986]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[3572418]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31056 Mentha haplocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. pericarp n.a. PMID[p25172756]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8650.3 Perilla frutescens (l.) britt. var. crispa (thunb.) hand.-mazz. Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31056 Mentha haplocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1880 Schizonepeta tenuisfolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25094 Artemisia princeps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2154 Ligusticum tenuissimum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15373 Actaea dahurica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10492 Artemisia montana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2727 Actaea simplex Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19048 Pinellia ternata Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15890 Cimicifuga foetida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19649 Akebia quinata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25094 Artemisia princeps 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 39810.7 nM PMID[523108]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[523109]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[523109]

☑ 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 NPC59570 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 NPC45270
1.0 High Similarity NPC135077
1.0 High Similarity NPC215118
0.8462 Intermediate Similarity NPC223315
0.8333 Intermediate Similarity NPC171783
0.8095 Intermediate Similarity NPC18397
0.7872 Intermediate Similarity NPC274182
0.7805 Intermediate Similarity NPC141634
0.7778 Intermediate Similarity NPC83187
0.7778 Intermediate Similarity NPC173996
0.7778 Intermediate Similarity NPC98246
0.7778 Intermediate Similarity NPC131981
0.7778 Intermediate Similarity NPC285814
0.7778 Intermediate Similarity NPC40249
0.7568 Intermediate Similarity NPC321646
0.75 Intermediate Similarity NPC236623
0.7447 Intermediate Similarity NPC293343
0.7447 Intermediate Similarity NPC258672
0.7447 Intermediate Similarity NPC247786
0.74 Intermediate Similarity NPC53245
0.74 Intermediate Similarity NPC288296
0.7317 Intermediate Similarity NPC69245
0.7297 Intermediate Similarity NPC153439
0.7297 Intermediate Similarity NPC79887
0.7297 Intermediate Similarity NPC196434
0.7297 Intermediate Similarity NPC29561
0.7297 Intermediate Similarity NPC221192
0.7297 Intermediate Similarity NPC42403
0.7297 Intermediate Similarity NPC4962
0.7297 Intermediate Similarity NPC222997
0.7255 Intermediate Similarity NPC200258
0.7255 Intermediate Similarity NPC184819
0.7255 Intermediate Similarity NPC307063
0.7234 Intermediate Similarity NPC294440
0.7234 Intermediate Similarity NPC20017
0.7115 Intermediate Similarity NPC151464
0.7115 Intermediate Similarity NPC474105
0.7115 Intermediate Similarity NPC143597
0.7105 Intermediate Similarity NPC168982
0.7027 Intermediate Similarity NPC38859
0.7027 Intermediate Similarity NPC295442
0.7027 Intermediate Similarity NPC198118
0.6981 Remote Similarity NPC115385
0.6923 Remote Similarity NPC149101
0.6923 Remote Similarity NPC225318
0.6923 Remote Similarity NPC268596
0.6923 Remote Similarity NPC76608
0.6923 Remote Similarity NPC16578
0.6852 Remote Similarity NPC127798
0.6829 Remote Similarity NPC218357
0.6757 Remote Similarity NPC100997
0.6727 Remote Similarity NPC472304
0.6727 Remote Similarity NPC276764
0.6667 Remote Similarity NPC192427
0.6667 Remote Similarity NPC14917
0.6667 Remote Similarity NPC4079
0.6667 Remote Similarity NPC236355
0.6607 Remote Similarity NPC270042
0.66 Remote Similarity NPC116906
0.6585 Remote Similarity NPC248190
0.6545 Remote Similarity NPC27610
0.6545 Remote Similarity NPC56905
0.6538 Remote Similarity NPC268564
0.6531 Remote Similarity NPC13105
0.6491 Remote Similarity NPC60565
0.6471 Remote Similarity NPC27438
0.6458 Remote Similarity NPC314679
0.6429 Remote Similarity NPC121215
0.6415 Remote Similarity NPC202850
0.6415 Remote Similarity NPC319589
0.6415 Remote Similarity NPC63396
0.641 Remote Similarity NPC158107
0.6379 Remote Similarity NPC472306
0.6316 Remote Similarity NPC127582
0.6279 Remote Similarity NPC301919
0.6271 Remote Similarity NPC128608
0.6271 Remote Similarity NPC469662
0.6271 Remote Similarity NPC285371
0.6271 Remote Similarity NPC475124
0.625 Remote Similarity NPC55023
0.6226 Remote Similarity NPC474141
0.6216 Remote Similarity NPC307594
0.6216 Remote Similarity NPC227197
0.6216 Remote Similarity NPC66624
0.6216 Remote Similarity NPC129976
0.62 Remote Similarity NPC91962
0.62 Remote Similarity NPC324793
0.62 Remote Similarity NPC477878
0.6182 Remote Similarity NPC20603
0.6167 Remote Similarity NPC469791
0.6102 Remote Similarity NPC197238
0.6102 Remote Similarity NPC202118
0.6102 Remote Similarity NPC165695
0.6098 Remote Similarity NPC49151
0.6098 Remote Similarity NPC179831
0.6098 Remote Similarity NPC254713
0.6098 Remote Similarity NPC262505
0.6098 Remote Similarity NPC261991
0.6071 Remote Similarity NPC193695
0.6071 Remote Similarity NPC55004
0.6071 Remote Similarity NPC49575
0.6071 Remote Similarity NPC230823
0.6071 Remote Similarity NPC267626
0.6066 Remote Similarity NPC189917
0.6066 Remote Similarity NPC96812
0.6066 Remote Similarity NPC103734
0.6066 Remote Similarity NPC168824
0.6066 Remote Similarity NPC107704
0.6066 Remote Similarity NPC43300
0.6066 Remote Similarity NPC323005
0.6066 Remote Similarity NPC39462
0.6053 Remote Similarity NPC79591
0.6034 Remote Similarity NPC478126
0.6 Remote Similarity NPC6697
0.6 Remote Similarity NPC275472
0.6 Remote Similarity NPC21844
0.5968 Remote Similarity NPC220210
0.5968 Remote Similarity NPC20181
0.5965 Remote Similarity NPC30215
0.5965 Remote Similarity NPC266295
0.5965 Remote Similarity NPC94991
0.5962 Remote Similarity NPC305182
0.5962 Remote Similarity NPC32351
0.5957 Remote Similarity NPC248763
0.5957 Remote Similarity NPC325452
0.5946 Remote Similarity NPC14312
0.5946 Remote Similarity NPC91093
0.5946 Remote Similarity NPC27501
0.5932 Remote Similarity NPC213152
0.5932 Remote Similarity NPC306750
0.5926 Remote Similarity NPC72722
0.5902 Remote Similarity NPC230047
0.5902 Remote Similarity NPC19311
0.5902 Remote Similarity NPC251118
0.5897 Remote Similarity NPC7777
0.5873 Remote Similarity NPC180777
0.5873 Remote Similarity NPC82477
0.5873 Remote Similarity NPC310992
0.5873 Remote Similarity NPC281203
0.5873 Remote Similarity NPC296697
0.5873 Remote Similarity NPC260319
0.5873 Remote Similarity NPC469724
0.5873 Remote Similarity NPC260474
0.5873 Remote Similarity NPC20610
0.5873 Remote Similarity NPC39157
0.5873 Remote Similarity NPC100917
0.5873 Remote Similarity NPC473225
0.5873 Remote Similarity NPC31187
0.5873 Remote Similarity NPC103647
0.5873 Remote Similarity NPC188292
0.5873 Remote Similarity NPC474954
0.5873 Remote Similarity NPC470956
0.5873 Remote Similarity NPC475977
0.5873 Remote Similarity NPC142754
0.5873 Remote Similarity NPC2568
0.587 Remote Similarity NPC3531
0.5862 Remote Similarity NPC285594
0.5862 Remote Similarity NPC96551
0.5862 Remote Similarity NPC259261
0.5862 Remote Similarity NPC143834
0.5849 Remote Similarity NPC291724
0.5849 Remote Similarity NPC274261
0.5849 Remote Similarity NPC314084
0.5814 Remote Similarity NPC49615
0.5806 Remote Similarity NPC84562
0.58 Remote Similarity NPC77550
0.58 Remote Similarity NPC108441
0.5781 Remote Similarity NPC6120
0.5781 Remote Similarity NPC182815
0.5781 Remote Similarity NPC213178
0.5781 Remote Similarity NPC474962
0.5781 Remote Similarity NPC139397
0.5781 Remote Similarity NPC477857
0.5781 Remote Similarity NPC327728
0.5781 Remote Similarity NPC286814
0.5781 Remote Similarity NPC131892
0.5781 Remote Similarity NPC324607
0.5781 Remote Similarity NPC321732
0.5763 Remote Similarity NPC25853
0.5763 Remote Similarity NPC40206
0.5741 Remote Similarity NPC22182
0.5738 Remote Similarity NPC212210
0.5714 Remote Similarity NPC287331
0.5714 Remote Similarity NPC144891
0.5714 Remote Similarity NPC302939
0.5714 Remote Similarity NPC41542
0.5714 Remote Similarity NPC263161
0.5714 Remote Similarity NPC472984
0.5692 Remote Similarity NPC108131
0.5692 Remote Similarity NPC282593
0.5692 Remote Similarity NPC307176
0.5692 Remote Similarity NPC260040
0.5692 Remote Similarity NPC214770
0.5692 Remote Similarity NPC477856
0.5692 Remote Similarity NPC163020
0.5692 Remote Similarity NPC251929
0.5692 Remote Similarity NPC2634
0.5692 Remote Similarity NPC40574
0.5692 Remote Similarity NPC476731
0.5692 Remote Similarity NPC265782

  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 NPC59570 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
0.7778 Intermediate Similarity NPD345 Approved
0.7778 Intermediate Similarity NPD344 Approved
0.7778 Intermediate Similarity NPD343 Approved
0.7059 Intermediate Similarity NPD615 Clinical (unspecified phase)
0.6458 Remote Similarity NPD634 Phase 3
0.617 Remote Similarity NPD387 Clinical (unspecified phase)
0.6167 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6136 Remote Similarity NPD9449 Clinical (unspecified phase)
0.6066 Remote Similarity NPD4224 Phase 2
0.6047 Remote Similarity NPD9447 Approved
0.5873 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5873 Remote Similarity NPD5360 Phase 3
0.5873 Remote Similarity NPD5361 Clinical (unspecified phase)
0.587 Remote Similarity NPD9450 Approved
0.587 Remote Similarity NPD77 Approved
0.58 Remote Similarity NPD386 Approved
0.58 Remote Similarity NPD388 Approved
0.5781 Remote Similarity NPD4137 Phase 3
0.5781 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5781 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5781 Remote Similarity NPD3698 Phase 2
0.5741 Remote Similarity NPD3186 Phase 1
0.5714 Remote Similarity NPD367 Approved
0.5692 Remote Similarity NPD4747 Approved
0.5692 Remote Similarity NPD4691 Approved
0.5692 Remote Similarity NPD4244 Approved
0.5692 Remote Similarity NPD4245 Approved
0.5692 Remote Similarity NPD4789 Approved
0.569 Remote Similarity NPD287 Approved
0.5686 Remote Similarity NPD384 Approved
0.5686 Remote Similarity NPD385 Approved
0.5606 Remote Similarity NPD4758 Discontinued
0.5606 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5606 Remote Similarity NPD6081 Approved
0.5606 Remote Similarity NPD5777 Approved
0.5606 Remote Similarity NPD4809 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