Structure

Physi-Chem Properties

Molecular Weight:  152.12
Volume:  182.397
LogP:  2.792
LogD:  1.761
LogS:  -2.382
# Rotatable Bonds:  4
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.344
Synthetic Accessibility Score:  2.876
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.311
MDCK Permeability:  2.7478467018227093e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.051
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.976
Plasma Protein Binding (PPB):  85.90045928955078%
Volume Distribution (VD):  2.515
Pgp-substrate:  16.397891998291016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.676
CYP1A2-substrate:  0.668
CYP2C19-inhibitor:  0.378
CYP2C19-substrate:  0.886
CYP2C9-inhibitor:  0.122
CYP2C9-substrate:  0.895
CYP2D6-inhibitor:  0.094
CYP2D6-substrate:  0.684
CYP3A4-inhibitor:  0.021
CYP3A4-substrate:  0.246

ADMET: Excretion

Clearance (CL):  3.461
Half-life (T1/2):  0.775

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.645
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.114
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.047
Skin Sensitization:  0.95
Carcinogencity:  0.76
Eye Corrosion:  0.96
Eye Irritation:  0.978
Respiratory Toxicity:  0.921

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

  Natural Product: NPC12319

Natural Product ID:  NPC12319
Common Name*:   3,7-Dimethylocta-2,6-Dienal
IUPAC Name:   3,7-dimethylocta-2,6-dienal
Synonyms:  
Standard InCHIKey:  WTEVQBCEXWBHNA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3
SMILES:  O=CC=C(CCC=C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2297541
PubChem CID:   8843
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001127] Acyclic 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
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO1064 Caesalpinia bonducella Species Fabaceae Eukaryota n.a. seed n.a. DOI[10.1016/S0040-4039(01)89961-5]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota Resin n.a. n.a. PMID[1294696]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[14510607]
NPO28935 Ericameria laricifolia Species Asteraceae Eukaryota n.a. Sonoran Desert n.a. PMID[15043404]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[15679319]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. fruit n.a. PMID[15739361]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[15987194]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota fruits n.a. n.a. PMID[16038540]
NPO14358 Rhodobacter sphaeroides Species Rhodobacteraceae Bacteria n.a. n.a. n.a. PMID[1612412]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[16441078]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[16621556]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[16945525]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17190459]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17580847]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[17689080]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[18177011]
NPO8068 Blumea mollis Species Asteraceae Eukaryota n.a. leaf n.a. PMID[18566831]
NPO21258 Sinularia dura Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[18630962]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. whole plant n.a. PMID[18771268]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. aerial part n.a. PMID[18991207]
NPO14162 Chlorophytum borivilianum Species Asparagaceae Eukaryota roots n.a. n.a. PMID[19128156]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[19271742]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota n.a. bark n.a. PMID[19329133]
NPO7016 Gardenia tubifera Species Rubiaceae Eukaryota exudate n.a. n.a. PMID[20028108]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[20590154]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20674349]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota essential oil Tibet n.a. PMID[20944522]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[21131198]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21338114]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[21428274]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. stem n.a. PMID[21428274]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. bark n.a. PMID[21875098]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[22272932]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. seed n.a. PMID[23845552]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[23872723]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota seeds n.a. n.a. PMID[23999046]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[24868863]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[25089845]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25193297]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25320841]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. fruit n.a. PMID[26169681]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[28541690]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[28682072]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[29883114]
NPO10230 Trichilia connaroides Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[31589431]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota Roots n.a. n.a. PMID[32004936]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[32996318]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8064299]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[9170290]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Fruit Juice n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26851 Eupatorium rebaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1079 Vachellia karroo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4004 Aquilegia ecalcarata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26851 Eupatorium rebaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18780 Diplacus aurantiacus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16703 Isodon lophanthoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8650 Perilla frutescens Species Lamiaceae 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]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10082 Citrus unshiu Species Rutaceae 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]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9546 Cinamomum cassia n.a. n.a. n.a. n.a. n.a. n.a. Database[TM-MC]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4554 Isatis tinctoria Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21771 Citrus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29377 Callistemon speciosus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13871 Solanum aphyodendron Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14057 Apollonias barbujana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7016 Gardenia tubifera Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8892 Sordaria araneosa Species Sordariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18780 Diplacus aurantiacus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16703 Isodon lophanthoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1064 Caesalpinia bonducella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14162 Chlorophytum borivilianum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4337 Gentiana kurroo Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19787 Citrus sinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO205 Lasianthus fordii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO144 Dysoxylum hainanense Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14358 Rhodobacter sphaeroides Species Rhodobacteraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12509 Dipterocarpus dyeri Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO634 Salvia divinorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4671 Persea mexicana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9344 Anisocycla jollyana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10230 Trichilia connaroides Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16079 Cephalaria leucantha Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27256 Solanum boerhaavii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15073 Cystoseira spinosa Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29411 Streptomyces nigrescens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29144 Ormosia fordiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5480 Mimosa aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8068 Blumea mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13766 Ceanothus velutinus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28935 Ericameria laricifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5270 Citrus natsudaidai Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27562 Coleus wulfenioides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9473 Aulacomnium palustre Species Aulacomniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26851 Eupatorium rebaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11998 Ledebouria socialis Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10124 Berberis heterobotrys Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9792 Leptospermum flavescens Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO746 Panax innovans Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28549 Mentha incana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14973 Ircinia felix Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29218 Ramalina farinacea Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26549 Polanisia trachysperma Species Cleomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10550 Artemisia hanseniana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29307 Loranthus longiflorus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4004 Aquilegia ecalcarata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21258 Sinularia dura Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28959 Cissus quadrangularis Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1079 Vachellia karroo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13467 Anarsia lineatella Species Gelechiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5191 Penicillium cinerascens Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO862 Podocarpus elatus Species Podocarpaceae 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 39.65 ug.mL-1 PMID[568463]
NPT165 Cell Line HeLa Homo sapiens GI = 60.0 % PMID[568463]
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27535.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 56031.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15484.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 31230.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 55537.1 nM PubChem BioAssay data set
NPT32 Organism Mus musculus Mus musculus Inhibition = 83.0 % PMID[568464]
NPT32 Organism Mus musculus Mus musculus Inhibition = 70.0 % PMID[568464]
NPT32 Organism Mus musculus Mus musculus Inhibition = 45.0 % PMID[568464]
NPT32 Organism Mus musculus Mus musculus Inhibition = 62.0 % PMID[568464]
NPT32 Organism Mus musculus Mus musculus Inhibition = 80.0 % PMID[568464]
NPT32 Organism Mus musculus Mus musculus Inhibition = 22.0 % PMID[568464]
NPT32 Organism Mus musculus Mus musculus Inhibition = 66.0 % PMID[568464]
NPT32 Organism Mus musculus Mus musculus Inhibition = 57.0 % PMID[568464]
NPT27 Others Unspecified TIME >= 0.5 hr PMID[568464]
NPT27 Others Unspecified Activity = 31.2 % PMID[568464]
NPT27 Others Unspecified Activity = 21.4 % PMID[568464]
NPT27 Others Unspecified Activity = 28.1 % PMID[568464]
NPT27 Others Unspecified Activity = 8.8 % PMID[568464]
NPT27 Others Unspecified Activity = 44.4 % PMID[568464]
NPT27 Others Unspecified Activity = 37.5 % PMID[568464]
NPT27 Others Unspecified Activity = 36.0 % PMID[568464]
NPT27 Others Unspecified Activity = 40.0 % PMID[568464]
NPT27 Others Unspecified Activity = 15.6 % PMID[568464]

☑ 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 NPC12319 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 NPC18205
0.8974 High Similarity NPC101147
0.875 High Similarity NPC33489
0.8718 High Similarity NPC33761
0.8684 High Similarity NPC279300
0.8684 High Similarity NPC254764
0.8537 High Similarity NPC298710
0.8537 High Similarity NPC287397
0.8537 High Similarity NPC208936
0.8537 High Similarity NPC67920
0.85 High Similarity NPC323278
0.8421 Intermediate Similarity NPC75204
0.8158 Intermediate Similarity NPC72258
0.7907 Intermediate Similarity NPC106819
0.7872 Intermediate Similarity NPC234829
0.7838 Intermediate Similarity NPC273054
0.7826 Intermediate Similarity NPC477789
0.775 Intermediate Similarity NPC8416
0.7632 Intermediate Similarity NPC109034
0.75 Intermediate Similarity NPC216921
0.7436 Intermediate Similarity NPC12889
0.7391 Intermediate Similarity NPC276009
0.7391 Intermediate Similarity NPC22098
0.7391 Intermediate Similarity NPC195246
0.7381 Intermediate Similarity NPC217923
0.7333 Intermediate Similarity NPC477686
0.7317 Intermediate Similarity NPC185839
0.7292 Intermediate Similarity NPC236338
0.7255 Intermediate Similarity NPC188789
0.725 Intermediate Similarity NPC269641
0.7234 Intermediate Similarity NPC324812
0.7209 Intermediate Similarity NPC111474
0.7179 Intermediate Similarity NPC266979
0.7174 Intermediate Similarity NPC270706
0.7174 Intermediate Similarity NPC191337
0.7143 Intermediate Similarity NPC180840
0.7143 Intermediate Similarity NPC30433
0.7111 Intermediate Similarity NPC301972
0.7073 Intermediate Similarity NPC38497
0.7059 Intermediate Similarity NPC209431
0.7059 Intermediate Similarity NPC100809
0.7021 Intermediate Similarity NPC128280
0.7 Intermediate Similarity NPC146507
0.6981 Remote Similarity NPC321568
0.6981 Remote Similarity NPC22019
0.6981 Remote Similarity NPC208749
0.6981 Remote Similarity NPC281986
0.6977 Remote Similarity NPC103213
0.6977 Remote Similarity NPC29091
0.6977 Remote Similarity NPC182840
0.6977 Remote Similarity NPC255042
0.6957 Remote Similarity NPC12907
0.6957 Remote Similarity NPC304079
0.6957 Remote Similarity NPC6963
0.6939 Remote Similarity NPC225974
0.6939 Remote Similarity NPC288381
0.6939 Remote Similarity NPC20934
0.6852 Remote Similarity NPC21946
0.6842 Remote Similarity NPC8466
0.6809 Remote Similarity NPC239754
0.6809 Remote Similarity NPC166788
0.6809 Remote Similarity NPC47946
0.6809 Remote Similarity NPC26600
0.675 Remote Similarity NPC144407
0.6735 Remote Similarity NPC145311
0.6727 Remote Similarity NPC82465
0.6667 Remote Similarity NPC8610
0.6667 Remote Similarity NPC471752
0.6667 Remote Similarity NPC197467
0.6667 Remote Similarity NPC163751
0.6667 Remote Similarity NPC269823
0.6667 Remote Similarity NPC44363
0.6667 Remote Similarity NPC100380
0.6667 Remote Similarity NPC308331
0.6667 Remote Similarity NPC262558
0.6667 Remote Similarity NPC110234
0.6604 Remote Similarity NPC317899
0.66 Remote Similarity NPC15325
0.66 Remote Similarity NPC15789
0.66 Remote Similarity NPC118788
0.6596 Remote Similarity NPC267514
0.6596 Remote Similarity NPC25771
0.6596 Remote Similarity NPC145755
0.6596 Remote Similarity NPC471753
0.6585 Remote Similarity NPC310810
0.6522 Remote Similarity NPC256766
0.6522 Remote Similarity NPC213538
0.6481 Remote Similarity NPC477790
0.6415 Remote Similarity NPC189677
0.6415 Remote Similarity NPC95581
0.641 Remote Similarity NPC123965
0.641 Remote Similarity NPC138113
0.641 Remote Similarity NPC115959
0.64 Remote Similarity NPC135698
0.64 Remote Similarity NPC267110
0.64 Remote Similarity NPC234597
0.6383 Remote Similarity NPC292463
0.6383 Remote Similarity NPC116934
0.6364 Remote Similarity NPC92863
0.6364 Remote Similarity NPC34873
0.6364 Remote Similarity NPC155880
0.6364 Remote Similarity NPC249850
0.6364 Remote Similarity NPC135863
0.6364 Remote Similarity NPC71755
0.6364 Remote Similarity NPC129150
0.6364 Remote Similarity NPC40434
0.6364 Remote Similarity NPC294938
0.6364 Remote Similarity NPC293437
0.6364 Remote Similarity NPC268185
0.6304 Remote Similarity NPC7754
0.6304 Remote Similarity NPC270170
0.6275 Remote Similarity NPC228776
0.6275 Remote Similarity NPC176819
0.6275 Remote Similarity NPC220191
0.6275 Remote Similarity NPC32351
0.6275 Remote Similarity NPC289388
0.6275 Remote Similarity NPC58970
0.6275 Remote Similarity NPC163984
0.6271 Remote Similarity NPC52449
0.6271 Remote Similarity NPC169275
0.625 Remote Similarity NPC60288
0.625 Remote Similarity NPC223679
0.625 Remote Similarity NPC114841
0.625 Remote Similarity NPC254095
0.625 Remote Similarity NPC138935
0.6226 Remote Similarity NPC23117
0.6226 Remote Similarity NPC14002
0.6226 Remote Similarity NPC474805
0.6226 Remote Similarity NPC37644
0.6226 Remote Similarity NPC296311
0.6222 Remote Similarity NPC15934
0.617 Remote Similarity NPC187922
0.6167 Remote Similarity NPC183422
0.6154 Remote Similarity NPC22329
0.6154 Remote Similarity NPC244452
0.6136 Remote Similarity NPC24833
0.6122 Remote Similarity NPC474362
0.6122 Remote Similarity NPC210560
0.6122 Remote Similarity NPC165651
0.6122 Remote Similarity NPC474202
0.6122 Remote Similarity NPC24824
0.6122 Remote Similarity NPC140501
0.6122 Remote Similarity NPC221379
0.6122 Remote Similarity NPC160628
0.6111 Remote Similarity NPC474127
0.6111 Remote Similarity NPC5626
0.6111 Remote Similarity NPC300121
0.6111 Remote Similarity NPC250539
0.6111 Remote Similarity NPC317796
0.6111 Remote Similarity NPC478120
0.6098 Remote Similarity NPC66577
0.6098 Remote Similarity NPC206088
0.6098 Remote Similarity NPC100879
0.6098 Remote Similarity NPC471327
0.6098 Remote Similarity NPC3649
0.6087 Remote Similarity NPC113082
0.6087 Remote Similarity NPC48930
0.6087 Remote Similarity NPC123357
0.6078 Remote Similarity NPC91765
0.6038 Remote Similarity NPC471751
0.6038 Remote Similarity NPC170167
0.6034 Remote Similarity NPC79756
0.6 Remote Similarity NPC297280
0.6 Remote Similarity NPC226511
0.5968 Remote Similarity NPC4370
0.5968 Remote Similarity NPC290350
0.5957 Remote Similarity NPC221250
0.5957 Remote Similarity NPC469713
0.5957 Remote Similarity NPC188596
0.5952 Remote Similarity NPC213749
0.5932 Remote Similarity NPC260573
0.5932 Remote Similarity NPC228574
0.5932 Remote Similarity NPC151648
0.5932 Remote Similarity NPC294304
0.5926 Remote Similarity NPC268564
0.5926 Remote Similarity NPC69898
0.5926 Remote Similarity NPC295777
0.5926 Remote Similarity NPC217188
0.5926 Remote Similarity NPC45283
0.5893 Remote Similarity NPC472808
0.5893 Remote Similarity NPC324224
0.5882 Remote Similarity NPC471958
0.5882 Remote Similarity NPC318549
0.5873 Remote Similarity NPC155198
0.587 Remote Similarity NPC277382
0.587 Remote Similarity NPC171978
0.5862 Remote Similarity NPC286189
0.5849 Remote Similarity NPC64866
0.5849 Remote Similarity NPC43053
0.5833 Remote Similarity NPC304151
0.5833 Remote Similarity NPC67761
0.5833 Remote Similarity NPC209279
0.5833 Remote Similarity NPC68889
0.5833 Remote Similarity NPC44343
0.5833 Remote Similarity NPC68110
0.5833 Remote Similarity NPC57923
0.5833 Remote Similarity NPC194586
0.5833 Remote Similarity NPC210303
0.5833 Remote Similarity NPC180871
0.5833 Remote Similarity NPC206906

  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 NPC12319 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
0.6977 Remote Similarity NPD5783 Phase 3
0.64 Remote Similarity NPD4220 Pre-registration
0.6154 Remote Similarity NPD6927 Phase 3
0.6122 Remote Similarity NPD4265 Approved
0.5918 Remote Similarity NPD6096 Approved
0.5918 Remote Similarity NPD6097 Approved
0.5882 Remote Similarity NPD5343 Approved
0.5789 Remote Similarity NPD8779 Phase 3
0.566 Remote Similarity NPD2268 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data