Structure

Physi-Chem Properties

Molecular Weight:  154.14
Volume:  179.114
LogP:  2.921
LogD:  2.963
LogS:  -2.378
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.575
Synthetic Accessibility Score:  3.611
Fsp3:  0.8
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:  -4.351
MDCK Permeability:  1.723226705507841e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.198
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.07
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.854
Plasma Protein Binding (PPB):  57.4268798828125%
Volume Distribution (VD):  1.459
Pgp-substrate:  43.89082336425781%

ADMET: Metabolism

CYP1A2-inhibitor:  0.381
CYP1A2-substrate:  0.759
CYP2C19-inhibitor:  0.086
CYP2C19-substrate:  0.83
CYP2C9-inhibitor:  0.048
CYP2C9-substrate:  0.755
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.564
CYP3A4-inhibitor:  0.024
CYP3A4-substrate:  0.226

ADMET: Excretion

Clearance (CL):  9.436
Half-life (T1/2):  0.476

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.269
Drug-inuced Liver Injury (DILI):  0.141
AMES Toxicity:  0.046
Rat Oral Acute Toxicity:  0.047
Maximum Recommended Daily Dose:  0.089
Skin Sensitization:  0.529
Carcinogencity:  0.412
Eye Corrosion:  0.952
Eye Irritation:  0.988
Respiratory Toxicity:  0.63

Download Data

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

  Natural Product: NPC67508

Natural Product ID:  NPC67508
Common Name*:   Isopulegol
IUPAC Name:   (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
Synonyms:   Isopulegol
Standard InCHIKey:  ZYTMANIQRDEHIO-KXUCPTDWSA-N
Standard InCHI:  InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
SMILES:  C=C(C)[C@@H]1CC[C@@H](C)C[C@H]1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL237994
PubChem CID:   170833
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
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10757717]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[10757728]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. PMID[11421740]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. PMID[11908993]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[11914965]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[12350165]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota Resin n.a. n.a. PMID[1294696]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. Okinawan, Japan n.a. PMID[14695804]
NPO28935 Ericameria laricifolia Species Asteraceae Eukaryota n.a. Sonoran Desert n.a. PMID[15043404]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[15332859]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. leaf n.a. PMID[15388977]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[15679319]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota Leaves the campus of Panjab University, Chandigarh, India PMID[16989303]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. stem n.a. PMID[17202689]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[17407351]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. PMID[17827010]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota stems and leaves n.a. n.a. PMID[18004816]
NPO20637 Piper acutifolium Species Piperaceae Eukaryota n.a. leaf n.a. PMID[18712933]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. aerial part n.a. PMID[18991207]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota n.a. bark n.a. PMID[19329133]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota Leaves; Stems n.a. n.a. PMID[19653667]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota fresh leaves and stems n.a. n.a. PMID[19653667]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. PMID[20488581]
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]
NPO30686 Citrus hystrix Species Rutaceae Eukaryota n.a. exocarp n.a. PMID[20964319]
NPO23499 Carpesium faberi Species Asteraceae Eukaryota whole plant Changshou County, Chongqing, China 2008-Aug PMID[21109433]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota Roots n.a. n.a. PMID[24054487]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24175626]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24412339]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota Essential oil n.a. n.a. PMID[24641242]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[25987373]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[27116034]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[28541690]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[29667821]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[7807132]
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]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10932 Melissa officinalis 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]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26851 Eupatorium rebaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5315 Zanthoxylum bungeanum 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]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22455 Corydalis sewerzowi Species Papaveraceae 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]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO319 Citrus limon Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO42012 Rosmarinus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26851 Eupatorium rebaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22455 Corydalis sewerzowi Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18780 Diplacus aurantiacus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1079 Vachellia karroo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27724 Polygala senega Species Polygalaceae 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]
NPO21963 Hypericum japonicum Species Hypericaceae 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]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO319 Citrus limon Species Rutaceae 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]
NPO24090 Aplysilla rosea Species Darwinellidae Eukaryota n.a. Austrila n.a. Database[Title]
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]
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]
NPO27724 Polygala senega Species Polygalaceae 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]
NPO23256 Mentha arvensis Species Lamiaceae 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]
NPO11169 Piper cubeba Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29218 Ramalina farinacea Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27256 Solanum boerhaavii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23924 Psilotum nudum Species Psilotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23459 Onoseris alata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23114 Cacalia robusta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24408 Ariocarpus fissuratus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20998 Machaerium kuhlmannii Species Dolichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28935 Ericameria laricifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23961 Scytonema ocellatum Species Scytonemataceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO23499 Carpesium faberi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27903 Delphinium denudatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23281 Aplysinella rhax Species Aplysinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22595 Trapa bicornis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26851 Eupatorium rebaudianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21963 Hypericum japonicum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23920 Amanita pseudoporphyria Species Amanitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22143 Genista sessilifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27883 Bursera simaruba Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23884 Hippobroma longiflora Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21827 Albatrellus caeruleoporus Species Albatrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1079 Vachellia karroo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24290 Claviceps microcephala Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29307 Loranthus longiflorus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23610 Aconitum tianschanicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23043 Cryptolestes pusillus Species Laemophloeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26549 Polanisia trachysperma Species Cleomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22324 Erium villosum Species Pseudococcidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29110 Litsea cubeba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO862 Podocarpus elatus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23545 Vellozia streptophylla Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24132 Euphausia superba Species Euphausiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28959 Cissus quadrangularis Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5782 Aniba rosaeodora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24445 Arbacia pustulosa Species Arbaciidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24090 Aplysilla rosea Species Darwinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23834 Chlamydomonas allensworthii Species Chlamydomonadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27724 Polygala senega Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29377 Callistemon speciosus Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24048 Cladonia pityrea Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23696 Solanum diflorum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21625 Bidens tripartita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19535 Senecio zoellneri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28549 Mentha incana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12429 Acicarpha tribuloides Species Calyceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18780 Diplacus aurantiacus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27562 Coleus wulfenioides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29144 Ormosia fordiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24005 Mytilus galloprovincialis Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23211 Xyris indica Species Xyridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24219 Erylus nobilis Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO738 Dahlstedtia pentaphylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20637 Piper acutifolium Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16043 Centaurea musimomum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24364 Petrosia corticata Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4010 Flemingia philippinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16079 Cephalaria leucantha Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17737 Lepidorhinus squamosus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13127 Vallaris heynei Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23792 Gomphostemma parviflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22455 Corydalis sewerzowi Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23413 Crematogaster africana Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8593 Zygosaccharomyces rouxii Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO319 Citrus limon Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23364 Lambertella corni Species Rutstroemiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23318 Aconitum palmatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29411 Streptomyces nigrescens Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18976 Centaurea arbutifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23739 Staehelina fruticosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24249 Codonopsis cordifolioidea Species Campanulaceae 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
NPO25443 NPC67508 Raw Fruit 0.3 0.1 0.5 mg/100g Database [DUKE]
NPO319 NPC67508 Raw Leaf Essent. Oil 4000 4000 4000 mg/100g Database [DUKE]
NPO42012 NPC67508 Other Plant 1.15 0.4 1.9 mg/100g Database [DUKE]
NPO10932 NPC67508 Other Shoot 4 1 7 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 282000.0 nM PMID[512743]
NPT20 Organism Candida albicans Candida albicans MIC > 200.0 ug.mL-1 PMID[512743]
NPT350 Organism Tetranychus urticae Tetranychus urticae LC50 = 29.0 microg/cm3 PMID[512744]
NPT350 Organism Tetranychus urticae Tetranychus urticae LC50 = 27.7 microg/cm3 PMID[512744]
NPT350 Organism Tetranychus urticae Tetranychus urticae LC50 = 30.1 microg/cm3 PMID[512744]
NPT350 Organism Tetranychus urticae Tetranychus urticae LC50 = 30.7 microg/cm3 PMID[512744]
NPT350 Organism Tetranychus urticae Tetranychus urticae LC50 = 30.3 microg/cm3 PMID[512744]
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv GI = 64.0 % PMID[512745]
NPT35 Others n.a. log K = 0.87 n.a. PMID[512745]

☑ 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 NPC67508 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 NPC84824
0.85 High Similarity NPC2728
0.85 High Similarity NPC282619
0.85 High Similarity NPC11555
0.85 High Similarity NPC60837
0.85 High Similarity NPC208198
0.85 High Similarity NPC172613
0.8361 Intermediate Similarity NPC473929
0.8333 Intermediate Similarity NPC101128
0.8333 Intermediate Similarity NPC144650
0.8235 Intermediate Similarity NPC87439
0.8148 Intermediate Similarity NPC251335
0.8077 Intermediate Similarity NPC147343
0.8077 Intermediate Similarity NPC176309
0.8077 Intermediate Similarity NPC198540
0.8077 Intermediate Similarity NPC223468
0.8077 Intermediate Similarity NPC287550
0.8077 Intermediate Similarity NPC84030
0.807 Intermediate Similarity NPC210316
0.8033 Intermediate Similarity NPC219940
0.8033 Intermediate Similarity NPC225415
0.8033 Intermediate Similarity NPC68656
0.7937 Intermediate Similarity NPC253303
0.7937 Intermediate Similarity NPC269077
0.7937 Intermediate Similarity NPC139207
0.7937 Intermediate Similarity NPC185874
0.7925 Intermediate Similarity NPC100445
0.7903 Intermediate Similarity NPC300442
0.7903 Intermediate Similarity NPC258595
0.7846 Intermediate Similarity NPC92801
0.7812 Intermediate Similarity NPC244790
0.7812 Intermediate Similarity NPC276616
0.7812 Intermediate Similarity NPC266578
0.7797 Intermediate Similarity NPC474769
0.7797 Intermediate Similarity NPC189290
0.7797 Intermediate Similarity NPC475830
0.7797 Intermediate Similarity NPC240206
0.7778 Intermediate Similarity NPC326310
0.7778 Intermediate Similarity NPC202017
0.7778 Intermediate Similarity NPC475897
0.7759 Intermediate Similarity NPC24443
0.7742 Intermediate Similarity NPC323424
0.7742 Intermediate Similarity NPC96793
0.7727 Intermediate Similarity NPC242992
0.7692 Intermediate Similarity NPC234511
0.7612 Intermediate Similarity NPC265485
0.7612 Intermediate Similarity NPC220939
0.7612 Intermediate Similarity NPC95165
0.7576 Intermediate Similarity NPC45296
0.7576 Intermediate Similarity NPC283316
0.7541 Intermediate Similarity NPC240506
0.7538 Intermediate Similarity NPC245795
0.7538 Intermediate Similarity NPC96484
0.7538 Intermediate Similarity NPC208999
0.7463 Intermediate Similarity NPC301226
0.7463 Intermediate Similarity NPC164022
0.7463 Intermediate Similarity NPC23954
0.7463 Intermediate Similarity NPC111234
0.7463 Intermediate Similarity NPC167706
0.7463 Intermediate Similarity NPC477792
0.7458 Intermediate Similarity NPC264779
0.7458 Intermediate Similarity NPC39068
0.7419 Intermediate Similarity NPC147524
0.7419 Intermediate Similarity NPC194208
0.7419 Intermediate Similarity NPC79576
0.7419 Intermediate Similarity NPC282694
0.7414 Intermediate Similarity NPC286752
0.7385 Intermediate Similarity NPC308522
0.7385 Intermediate Similarity NPC74885
0.7377 Intermediate Similarity NPC122239
0.7353 Intermediate Similarity NPC211009
0.7353 Intermediate Similarity NPC182717
0.7344 Intermediate Similarity NPC471200
0.7313 Intermediate Similarity NPC145498
0.7288 Intermediate Similarity NPC148216
0.7288 Intermediate Similarity NPC251666
0.7288 Intermediate Similarity NPC232247
0.7288 Intermediate Similarity NPC130209
0.7288 Intermediate Similarity NPC148163
0.7286 Intermediate Similarity NPC265588
0.7258 Intermediate Similarity NPC66020
0.7246 Intermediate Similarity NPC145552
0.7246 Intermediate Similarity NPC62657
0.7246 Intermediate Similarity NPC100334
0.7246 Intermediate Similarity NPC254509
0.7246 Intermediate Similarity NPC243342
0.7246 Intermediate Similarity NPC196358
0.7246 Intermediate Similarity NPC5046
0.7246 Intermediate Similarity NPC25511
0.7246 Intermediate Similarity NPC308440
0.7246 Intermediate Similarity NPC472503
0.7246 Intermediate Similarity NPC192638
0.7246 Intermediate Similarity NPC477138
0.7246 Intermediate Similarity NPC49168
0.7231 Intermediate Similarity NPC267027
0.7206 Intermediate Similarity NPC110799
0.7206 Intermediate Similarity NPC242001
0.7193 Intermediate Similarity NPC307022
0.7188 Intermediate Similarity NPC290367
0.7183 Intermediate Similarity NPC91594
0.7183 Intermediate Similarity NPC471798
0.717 Intermediate Similarity NPC144891
0.7164 Intermediate Similarity NPC474248
0.7164 Intermediate Similarity NPC9942
0.7164 Intermediate Similarity NPC210323
0.7143 Intermediate Similarity NPC68679
0.7143 Intermediate Similarity NPC291503
0.7143 Intermediate Similarity NPC225342
0.7143 Intermediate Similarity NPC230704
0.7143 Intermediate Similarity NPC104387
0.7143 Intermediate Similarity NPC477923
0.7143 Intermediate Similarity NPC231256
0.7143 Intermediate Similarity NPC66566
0.7143 Intermediate Similarity NPC144075
0.7143 Intermediate Similarity NPC121744
0.7143 Intermediate Similarity NPC3403
0.7143 Intermediate Similarity NPC212879
0.7143 Intermediate Similarity NPC207007
0.7143 Intermediate Similarity NPC118508
0.7143 Intermediate Similarity NPC240235
0.7143 Intermediate Similarity NPC321867
0.7143 Intermediate Similarity NPC70982
0.7143 Intermediate Similarity NPC178383
0.7143 Intermediate Similarity NPC185536
0.7143 Intermediate Similarity NPC200243
0.7143 Intermediate Similarity NPC322353
0.7121 Intermediate Similarity NPC114651
0.7121 Intermediate Similarity NPC476650
0.7121 Intermediate Similarity NPC82337
0.7119 Intermediate Similarity NPC53209
0.7101 Intermediate Similarity NPC195489
0.7101 Intermediate Similarity NPC471799
0.7083 Intermediate Similarity NPC22955
0.7083 Intermediate Similarity NPC470396
0.7083 Intermediate Similarity NPC474989
0.7083 Intermediate Similarity NPC52755
0.7083 Intermediate Similarity NPC99168
0.7083 Intermediate Similarity NPC275910
0.7077 Intermediate Similarity NPC27243
0.7077 Intermediate Similarity NPC476737
0.7077 Intermediate Similarity NPC287339
0.7077 Intermediate Similarity NPC64123
0.7069 Intermediate Similarity NPC179169
0.7069 Intermediate Similarity NPC157781
0.7069 Intermediate Similarity NPC306195
0.7069 Intermediate Similarity NPC181255
0.7069 Intermediate Similarity NPC35519
0.7059 Intermediate Similarity NPC34834
0.7042 Intermediate Similarity NPC122418
0.7042 Intermediate Similarity NPC240604
0.7042 Intermediate Similarity NPC30590
0.7042 Intermediate Similarity NPC106364
0.7042 Intermediate Similarity NPC189883
0.7042 Intermediate Similarity NPC290598
0.7042 Intermediate Similarity NPC46160
0.7042 Intermediate Similarity NPC300324
0.7042 Intermediate Similarity NPC202642
0.7042 Intermediate Similarity NPC265328
0.7042 Intermediate Similarity NPC237460
0.7042 Intermediate Similarity NPC278091
0.7042 Intermediate Similarity NPC14112
0.7042 Intermediate Similarity NPC91573
0.7042 Intermediate Similarity NPC63958
0.7042 Intermediate Similarity NPC73875
0.7042 Intermediate Similarity NPC86305
0.7042 Intermediate Similarity NPC78067
0.7042 Intermediate Similarity NPC27765
0.7042 Intermediate Similarity NPC93662
0.7042 Intermediate Similarity NPC120098
0.7031 Intermediate Similarity NPC83200
0.7031 Intermediate Similarity NPC279200
0.7031 Intermediate Similarity NPC473508
0.7015 Intermediate Similarity NPC471238
0.7015 Intermediate Similarity NPC2648
0.7 Intermediate Similarity NPC71152
0.7 Intermediate Similarity NPC201048
0.7 Intermediate Similarity NPC91858
0.7 Intermediate Similarity NPC471797
0.7 Intermediate Similarity NPC476366
0.6986 Remote Similarity NPC53744
0.6986 Remote Similarity NPC5604
0.6986 Remote Similarity NPC472463
0.6986 Remote Similarity NPC281138
0.6986 Remote Similarity NPC291379
0.6984 Remote Similarity NPC99487
0.697 Remote Similarity NPC476406
0.697 Remote Similarity NPC272125
0.6957 Remote Similarity NPC469343
0.6957 Remote Similarity NPC471268
0.6957 Remote Similarity NPC471272
0.6957 Remote Similarity NPC164045
0.6957 Remote Similarity NPC471271
0.6944 Remote Similarity NPC212241
0.6944 Remote Similarity NPC202540
0.6944 Remote Similarity NPC257191
0.6944 Remote Similarity NPC119355
0.6944 Remote Similarity NPC214570
0.6944 Remote Similarity NPC138502
0.6944 Remote Similarity NPC90979
0.6944 Remote Similarity NPC477924

  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 NPC67508 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
0.8077 Intermediate Similarity NPD384 Approved
0.8077 Intermediate Similarity NPD385 Approved
0.7288 Intermediate Similarity NPD342 Phase 1
0.7143 Intermediate Similarity NPD368 Approved
0.6901 Remote Similarity NPD7339 Approved
0.6901 Remote Similarity NPD6942 Approved
0.6806 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6761 Remote Similarity NPD6924 Approved
0.6761 Remote Similarity NPD6926 Approved
0.6757 Remote Similarity NPD7645 Phase 2
0.6719 Remote Similarity NPD1145 Discontinued
0.6667 Remote Similarity NPD7525 Registered
0.6667 Remote Similarity NPD6922 Approved
0.6667 Remote Similarity NPD6923 Approved
0.6575 Remote Similarity NPD6933 Approved
0.6571 Remote Similarity NPD7144 Approved
0.6571 Remote Similarity NPD7143 Approved
0.6552 Remote Similarity NPD9410 Clinical (unspecified phase)
0.6479 Remote Similarity NPD7151 Approved
0.6479 Remote Similarity NPD7150 Approved
0.6479 Remote Similarity NPD7152 Approved
0.6447 Remote Similarity NPD7509 Discontinued
0.6316 Remote Similarity NPD386 Approved
0.6316 Remote Similarity NPD6929 Approved
0.6316 Remote Similarity NPD388 Approved
0.6282 Remote Similarity NPD3667 Approved
0.625 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6234 Remote Similarity NPD6931 Approved
0.6234 Remote Similarity NPD4748 Discontinued
0.6234 Remote Similarity NPD6930 Phase 2
0.6216 Remote Similarity NPD8264 Approved
0.6176 Remote Similarity NPD371 Approved
0.6173 Remote Similarity NPD3618 Phase 1
0.6125 Remote Similarity NPD4786 Approved
0.6081 Remote Similarity NPD4784 Approved
0.6081 Remote Similarity NPD4785 Approved
0.6053 Remote Similarity NPD5776 Phase 2
0.6053 Remote Similarity NPD6925 Approved
0.6053 Remote Similarity NPD6932 Approved
0.6027 Remote Similarity NPD4243 Approved
0.6 Remote Similarity NPD6695 Phase 3
0.5974 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5974 Remote Similarity NPD7145 Approved
0.5952 Remote Similarity NPD5328 Approved
0.5926 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5926 Remote Similarity NPD3133 Approved
0.5926 Remote Similarity NPD3665 Phase 1
0.5926 Remote Similarity NPD3666 Approved
0.5904 Remote Similarity NPD4751 Clinical (unspecified phase)
0.5897 Remote Similarity NPD6683 Phase 2
0.5854 Remote Similarity NPD6893 Approved
0.5823 Remote Similarity NPD7332 Phase 2
0.5823 Remote Similarity NPD7514 Phase 3
0.5814 Remote Similarity NPD6079 Approved
0.5814 Remote Similarity NPD7515 Phase 2
0.5802 Remote Similarity NPD4788 Approved
0.5789 Remote Similarity NPD1462 Approved
0.5789 Remote Similarity NPD5275 Approved
0.5789 Remote Similarity NPD4190 Phase 3
0.5753 Remote Similarity NPD4267 Clinical (unspecified phase)
0.575 Remote Similarity NPD6898 Phase 1
0.575 Remote Similarity NPD6902 Approved
0.5747 Remote Similarity NPD4202 Approved
0.5733 Remote Similarity NPD4732 Discontinued
0.5714 Remote Similarity NPD1460 Approved
0.5714 Remote Similarity NPD7750 Discontinued
0.5714 Remote Similarity NPD7524 Approved
0.5634 Remote Similarity NPD7341 Phase 2
0.5632 Remote Similarity NPD8034 Phase 2
0.5632 Remote Similarity NPD8035 Phase 2
0.5606 Remote Similarity NPD4219 Approved

  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