Structure

Physi-Chem Properties

Molecular Weight:  152.12
Volume:  176.477
LogP:  2.139
LogD:  1.538
LogS:  -2.073
# Rotatable Bonds:  1
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.564
Synthetic Accessibility Score:  3.254
Fsp3:  0.7
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:  -4.362
MDCK Permeability:  2.858364678104408e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.151

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.906
Plasma Protein Binding (PPB):  89.33605194091797%
Volume Distribution (VD):  1.031
Pgp-substrate:  10.14136791229248%

ADMET: Metabolism

CYP1A2-inhibitor:  0.359
CYP1A2-substrate:  0.789
CYP2C19-inhibitor:  0.351
CYP2C19-substrate:  0.93
CYP2C9-inhibitor:  0.212
CYP2C9-substrate:  0.839
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.673
CYP3A4-inhibitor:  0.071
CYP3A4-substrate:  0.603

ADMET: Excretion

Clearance (CL):  5.322
Half-life (T1/2):  0.693

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.158
Drug-inuced Liver Injury (DILI):  0.082
AMES Toxicity:  0.032
Rat Oral Acute Toxicity:  0.043
Maximum Recommended Daily Dose:  0.081
Skin Sensitization:  0.788
Carcinogencity:  0.612
Eye Corrosion:  0.888
Eye Irritation:  0.981
Respiratory Toxicity:  0.786

Download Data

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

  Natural Product: NPC268564

Natural Product ID:  NPC268564
Common Name*:   (-)-Piperitone
IUPAC Name:   (6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
Synonyms:  
Standard InCHIKey:  YSTPAHQEHQSRJD-SECBINFHSA-N
Standard InCHI:  InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m1/s1
SMILES:  CC(C)[C@H]1CCC(=CC1=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2229207
PubChem CID:   107561
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
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. DOI[10.1016/0045-6535(91)90110-Y]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(00)94055-X]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4039(01)00209-X]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. flower n.a. DOI[10.3390/70200245]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[10575373]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[12088434]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[12776552]
NPO3799 Philinopsis speciosa Species Aglajidae Eukaryota n.a. n.a. n.a. PMID[15332851]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[15387651]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. leaf n.a. PMID[15388977]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. leaf n.a. PMID[15467205]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[15679319]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. whole plant n.a. PMID[16808005]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. stem n.a. PMID[17202689]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. seed n.a. PMID[17345316]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. aerial part n.a. PMID[18991207]
NPO27786 Eucalyptus dives Species Myrtaceae Eukaryota essential oils n.a. n.a. PMID[19191669]
NPO33171 matricaria recutita Species Asteraceae Eukaryota essential oils n.a. n.a. PMID[19191669]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota stem bark n.a. n.a. PMID[20411974]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota roots and rhizomes Shaoguan, Guangdong Province, China 2007-Dec PMID[20540535]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. pericarp n.a. PMID[20628994]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota essential oil Tibet n.a. PMID[20944522]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21428416]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21707257]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. exocarp n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. root n.a. PMID[21800857]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22870812]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23102654]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23435948]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24175626]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24617303]
NPO5652 Barleria lupulina Species Acanthaceae Eukaryota aerial part purchased in Vung Tau, Vietnam 2012-MAR PMID[25611215]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[25737008]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. PMID[27439360]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[28541690]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[31103896]
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]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO28928 Piper nigrum Species Piperaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota Leaf 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]
NPO163 Daucus carota Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Tissue Culture 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 n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26495 Cymbopogon sennaarensis Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO695 Picea sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23814 Elsholtzia splendens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22596 Semen artemisiae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31056 Mentha haplocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27786 Eucalyptus dives Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5652 Barleria lupulina Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12441 Cymbopogon distans Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30300 Gallus domesticus Species Phasianidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26495 Cymbopogon sennaarensis Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO695 Picea sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12441 Cymbopogon distans Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23814 Elsholtzia splendens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22596 Semen artemisiae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5652 Barleria lupulina Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15634 Radix smilacis Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27786 Eucalyptus dives Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5315 Zanthoxylum bungeanum Species Rutaceae 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]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11100 Artemisia capillaris Species Asteraceae 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]
NPO12441 Cymbopogon distans Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28295 Foeniculum vulgare Species Apiaceae 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]
NPO28260 Senna alexandrina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11871 Illicium difengpi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17295 Chrysanthemum zawadskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28928 Piper nigrum Species Piperaceae 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]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO163 Daucus carota Species Apiaceae 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]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9290 Zanthoxylum piperitum Species Rutaceae 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]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27786 Eucalyptus dives Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5652 Barleria lupulina Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23814 Elsholtzia splendens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27364 Gallus gallus Species Phasianidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3799 Philinopsis speciosa Species Aglajidae 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]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17295 Chrysanthemum zawadskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO695 Picea sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6613 Casimiroa pubescens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1908 Isolona hexaloba Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29110 Litsea cubeba Species Lauraceae 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
NPO14579 NPC268564 Other Leaf 31.2 2.4 60 mg/100g Database [DUKE]
NPO23256 NPC268564 Other Leaf 397 24 770 mg/100g Database [DUKE]

☑ 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
NPT1276 Organism Gibberella zeae Gibberella zeae Inhibition = 25.0 % PMID[534686]
NPT1276 Organism Gibberella zeae Gibberella zeae Inhibition = 20.0 % PMID[534686]
NPT1276 Organism Gibberella zeae Gibberella zeae IC50 = 61.2 ppm PMID[534686]
NPT1276 Organism Gibberella zeae Gibberella zeae IC50 = 306000.0 nM PMID[534686]

☑ 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 NPC268564 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
0.9388 High Similarity NPC32351
0.9 High Similarity NPC163984
0.9 High Similarity NPC176819
0.9 High Similarity NPC58970
0.898 High Similarity NPC91962
0.8909 High Similarity NPC472304
0.8909 High Similarity NPC276764
0.8727 High Similarity NPC170799
0.8727 High Similarity NPC308108
0.8545 High Similarity NPC115385
0.8462 Intermediate Similarity NPC64866
0.8462 Intermediate Similarity NPC27438
0.8448 Intermediate Similarity NPC165695
0.8421 Intermediate Similarity NPC127582
0.84 Intermediate Similarity NPC4079
0.84 Intermediate Similarity NPC236355
0.84 Intermediate Similarity NPC14917
0.8393 Intermediate Similarity NPC27610
0.8393 Intermediate Similarity NPC56905
0.8393 Intermediate Similarity NPC311852
0.8367 Intermediate Similarity NPC25771
0.8364 Intermediate Similarity NPC473733
0.8305 Intermediate Similarity NPC475124
0.8305 Intermediate Similarity NPC6697
0.8305 Intermediate Similarity NPC285371
0.8276 Intermediate Similarity NPC213152
0.8214 Intermediate Similarity NPC193695
0.8182 Intermediate Similarity NPC275472
0.8167 Intermediate Similarity NPC251118
0.8163 Intermediate Similarity NPC292463
0.8148 Intermediate Similarity NPC45283
0.8148 Intermediate Similarity NPC23117
0.8148 Intermediate Similarity NPC474141
0.807 Intermediate Similarity NPC266295
0.807 Intermediate Similarity NPC94991
0.8039 Intermediate Similarity NPC8610
0.8039 Intermediate Similarity NPC262558
0.8036 Intermediate Similarity NPC20603
0.8 Intermediate Similarity NPC5626
0.8 Intermediate Similarity NPC100809
0.8 Intermediate Similarity NPC63396
0.8 Intermediate Similarity NPC202850
0.8 Intermediate Similarity NPC212210
0.8 Intermediate Similarity NPC209431
0.7963 Intermediate Similarity NPC471751
0.7931 Intermediate Similarity NPC143834
0.7931 Intermediate Similarity NPC259261
0.7931 Intermediate Similarity NPC96551
0.7931 Intermediate Similarity NPC285594
0.7925 Intermediate Similarity NPC228776
0.7869 Intermediate Similarity NPC470329
0.7843 Intermediate Similarity NPC166788
0.7833 Intermediate Similarity NPC32285
0.7833 Intermediate Similarity NPC288253
0.7818 Intermediate Similarity NPC14002
0.7818 Intermediate Similarity NPC37644
0.7797 Intermediate Similarity NPC25853
0.7778 Intermediate Similarity NPC260474
0.7778 Intermediate Similarity NPC310992
0.7778 Intermediate Similarity NPC87141
0.7778 Intermediate Similarity NPC188292
0.7759 Intermediate Similarity NPC30215
0.7705 Intermediate Similarity NPC150162
0.7705 Intermediate Similarity NPC469662
0.7667 Intermediate Similarity NPC60565
0.7656 Intermediate Similarity NPC139397
0.7656 Intermediate Similarity NPC256846
0.7619 Intermediate Similarity NPC475523
0.7593 Intermediate Similarity NPC116906
0.7586 Intermediate Similarity NPC267626
0.7586 Intermediate Similarity NPC49575
0.7586 Intermediate Similarity NPC230823
0.7586 Intermediate Similarity NPC192427
0.7586 Intermediate Similarity NPC55004
0.7544 Intermediate Similarity NPC200258
0.7541 Intermediate Similarity NPC202118
0.7541 Intermediate Similarity NPC197238
0.7538 Intermediate Similarity NPC251929
0.7538 Intermediate Similarity NPC159577
0.7538 Intermediate Similarity NPC2634
0.7538 Intermediate Similarity NPC260040
0.7538 Intermediate Similarity NPC282593
0.7538 Intermediate Similarity NPC307176
0.7538 Intermediate Similarity NPC35734
0.7538 Intermediate Similarity NPC265782
0.75 Intermediate Similarity NPC296311
0.75 Intermediate Similarity NPC155198
0.75 Intermediate Similarity NPC191337
0.7455 Intermediate Similarity NPC236623
0.7451 Intermediate Similarity NPC301972
0.7424 Intermediate Similarity NPC54123
0.7424 Intermediate Similarity NPC474562
0.7424 Intermediate Similarity NPC190035
0.7424 Intermediate Similarity NPC115023
0.7419 Intermediate Similarity NPC473902
0.7419 Intermediate Similarity NPC4638
0.7407 Intermediate Similarity NPC145311
0.7385 Intermediate Similarity NPC474060
0.7377 Intermediate Similarity NPC475795
0.7377 Intermediate Similarity NPC97322
0.7358 Intermediate Similarity NPC276009
0.7358 Intermediate Similarity NPC22098
0.7358 Intermediate Similarity NPC100380
0.7358 Intermediate Similarity NPC195246
0.7344 Intermediate Similarity NPC4370
0.7344 Intermediate Similarity NPC290350
0.7313 Intermediate Similarity NPC180015
0.7313 Intermediate Similarity NPC470044
0.7313 Intermediate Similarity NPC251705
0.7313 Intermediate Similarity NPC303613
0.7313 Intermediate Similarity NPC56747
0.7313 Intermediate Similarity NPC130016
0.7313 Intermediate Similarity NPC474228
0.7313 Intermediate Similarity NPC470045
0.7313 Intermediate Similarity NPC109576
0.7308 Intermediate Similarity NPC477686
0.7288 Intermediate Similarity NPC165808
0.7273 Intermediate Similarity NPC246722
0.7273 Intermediate Similarity NPC151045
0.7273 Intermediate Similarity NPC15325
0.7273 Intermediate Similarity NPC118788
0.7258 Intermediate Similarity NPC472306
0.7258 Intermediate Similarity NPC167256
0.7241 Intermediate Similarity NPC188789
0.7231 Intermediate Similarity NPC82477
0.7231 Intermediate Similarity NPC142754
0.7231 Intermediate Similarity NPC296697
0.7231 Intermediate Similarity NPC20610
0.7231 Intermediate Similarity NPC39157
0.7193 Intermediate Similarity NPC295777
0.7193 Intermediate Similarity NPC69898
0.7188 Intermediate Similarity NPC323005
0.7167 Intermediate Similarity NPC60772
0.7164 Intermediate Similarity NPC5701
0.7164 Intermediate Similarity NPC225467
0.7164 Intermediate Similarity NPC234707
0.7164 Intermediate Similarity NPC181204
0.7143 Intermediate Similarity NPC214584
0.7143 Intermediate Similarity NPC26906
0.7121 Intermediate Similarity NPC469914
0.7121 Intermediate Similarity NPC286814
0.7121 Intermediate Similarity NPC182815
0.7119 Intermediate Similarity NPC141699
0.7101 Intermediate Similarity NPC473171
0.7101 Intermediate Similarity NPC65650
0.7101 Intermediate Similarity NPC476346
0.7101 Intermediate Similarity NPC293803
0.7077 Intermediate Similarity NPC20181
0.7077 Intermediate Similarity NPC220210
0.7069 Intermediate Similarity NPC250539
0.7037 Intermediate Similarity NPC471752
0.7018 Intermediate Similarity NPC306195
0.7018 Intermediate Similarity NPC157781
0.7018 Intermediate Similarity NPC181255
0.7018 Intermediate Similarity NPC71506
0.7018 Intermediate Similarity NPC179169
0.7018 Intermediate Similarity NPC35519
0.7018 Intermediate Similarity NPC177112
0.7 Intermediate Similarity NPC69408
0.7 Intermediate Similarity NPC151622
0.7 Intermediate Similarity NPC1254
0.7 Intermediate Similarity NPC7629
0.7 Intermediate Similarity NPC180886
0.7 Intermediate Similarity NPC472305
0.7 Intermediate Similarity NPC186554
0.7 Intermediate Similarity NPC76966
0.697 Remote Similarity NPC469688
0.697 Remote Similarity NPC469679
0.6957 Remote Similarity NPC474796
0.6957 Remote Similarity NPC474797
0.6957 Remote Similarity NPC309852
0.6957 Remote Similarity NPC329866
0.6957 Remote Similarity NPC255021
0.6939 Remote Similarity NPC185839
0.6939 Remote Similarity NPC76145
0.6939 Remote Similarity NPC34764
0.6939 Remote Similarity NPC190810
0.6923 Remote Similarity NPC197089
0.6923 Remote Similarity NPC176171
0.6923 Remote Similarity NPC92327
0.6912 Remote Similarity NPC305501
0.6912 Remote Similarity NPC304983
0.6912 Remote Similarity NPC21944
0.6912 Remote Similarity NPC133253
0.6912 Remote Similarity NPC470078
0.6901 Remote Similarity NPC266193
0.6901 Remote Similarity NPC34110
0.6901 Remote Similarity NPC257666
0.6901 Remote Similarity NPC197659
0.6901 Remote Similarity NPC472300
0.6866 Remote Similarity NPC136473
0.6866 Remote Similarity NPC61702
0.6866 Remote Similarity NPC162867
0.6863 Remote Similarity NPC111474
0.6863 Remote Similarity NPC113082
0.6857 Remote Similarity NPC114236
0.6818 Remote Similarity NPC193770
0.6818 Remote Similarity NPC176107
0.6812 Remote Similarity NPC186042
0.6812 Remote Similarity NPC474488

  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 NPC268564 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
0.8727 High Similarity NPD287 Approved
0.7656 Intermediate Similarity NPD4137 Phase 3
0.7538 Intermediate Similarity NPD4691 Approved
0.7538 Intermediate Similarity NPD4747 Approved
0.7231 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD4058 Approved
0.7206 Intermediate Similarity NPD4687 Approved
0.7206 Intermediate Similarity NPD5733 Approved
0.7188 Intermediate Similarity NPD7331 Phase 2
0.7164 Intermediate Similarity NPD5276 Approved
0.6939 Remote Similarity NPD319 Phase 1
0.6769 Remote Similarity NPD7341 Phase 2
0.6667 Remote Similarity NPD5783 Phase 3
0.6447 Remote Similarity NPD4223 Phase 3
0.6447 Remote Similarity NPD4221 Approved
0.64 Remote Similarity NPD4695 Discontinued
0.6393 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6316 Remote Similarity NPD8028 Phase 2
0.6282 Remote Similarity NPD4197 Approved
0.6282 Remote Similarity NPD3133 Approved
0.6282 Remote Similarity NPD3665 Phase 1
0.6282 Remote Similarity NPD3666 Approved
0.6212 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6203 Remote Similarity NPD5329 Approved
0.6176 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6133 Remote Similarity NPD3617 Approved
0.6125 Remote Similarity NPD4693 Phase 3
0.6125 Remote Similarity NPD7521 Approved
0.6125 Remote Similarity NPD5690 Phase 2
0.6125 Remote Similarity NPD5280 Approved
0.6125 Remote Similarity NPD4694 Approved
0.6125 Remote Similarity NPD5330 Approved
0.6125 Remote Similarity NPD4623 Approved
0.6125 Remote Similarity NPD4689 Approved
0.6125 Remote Similarity NPD4519 Discontinued
0.6125 Remote Similarity NPD7146 Approved
0.6125 Remote Similarity NPD7334 Approved
0.6125 Remote Similarity NPD6409 Approved
0.6125 Remote Similarity NPD3618 Phase 1
0.6125 Remote Similarity NPD5205 Approved
0.6125 Remote Similarity NPD4688 Approved
0.6125 Remote Similarity NPD4138 Approved
0.6125 Remote Similarity NPD6684 Approved
0.6125 Remote Similarity NPD4690 Approved
0.6061 Remote Similarity NPD368 Approved
0.6061 Remote Similarity NPD4194 Approved
0.6061 Remote Similarity NPD4193 Approved
0.6061 Remote Similarity NPD4191 Approved
0.6061 Remote Similarity NPD4192 Approved
0.6049 Remote Similarity NPD3573 Approved
0.6026 Remote Similarity NPD3667 Approved
0.6 Remote Similarity NPD1694 Approved
0.5976 Remote Similarity NPD6903 Approved
0.5976 Remote Similarity NPD6672 Approved
0.5976 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5976 Remote Similarity NPD5208 Approved
0.5976 Remote Similarity NPD5737 Approved
0.5974 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5938 Remote Similarity NPD8779 Phase 3
0.5926 Remote Similarity NPD5279 Phase 3
0.5926 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5904 Remote Similarity NPD5328 Approved
0.5904 Remote Similarity NPD4753 Phase 2
0.5904 Remote Similarity NPD6080 Approved
0.5904 Remote Similarity NPD6904 Approved
0.5904 Remote Similarity NPD6673 Approved
0.5875 Remote Similarity NPD4786 Approved
0.5875 Remote Similarity NPD3668 Phase 3
0.5873 Remote Similarity NPD342 Phase 1
0.5844 Remote Similarity NPD4195 Approved
0.5833 Remote Similarity NPD5207 Approved
0.5833 Remote Similarity NPD5692 Phase 3
0.5783 Remote Similarity NPD4518 Approved
0.5765 Remote Similarity NPD5694 Approved
0.5765 Remote Similarity NPD6050 Approved
0.5765 Remote Similarity NPD5281 Approved
0.5765 Remote Similarity NPD6079 Approved
0.5765 Remote Similarity NPD5284 Approved
0.5765 Remote Similarity NPD7515 Phase 2
0.5765 Remote Similarity NPD5693 Phase 1
0.5732 Remote Similarity NPD6098 Approved
0.5714 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5714 Remote Similarity NPD1799 Clinical (unspecified phase)
0.5698 Remote Similarity NPD7631 Approved
0.5698 Remote Similarity NPD4202 Approved
0.569 Remote Similarity NPD3174 Discontinued
0.5647 Remote Similarity NPD4096 Approved
0.5632 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5632 Remote Similarity NPD7900 Approved
0.5632 Remote Similarity NPD7748 Approved
0.5632 Remote Similarity NPD6001 Approved
0.5625 Remote Similarity NPD4752 Clinical (unspecified phase)
0.561 Remote Similarity NPD1696 Phase 3

  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