Structure

Physi-Chem Properties

Molecular Weight:  102.07
Volume:  109.98
LogP:  1.269
LogD:  2.241
LogS:  -0.35
# Rotatable Bonds:  2
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.567
Synthetic Accessibility Score:  2.51
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:  -4.65
MDCK Permeability:  9.951391257345676e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.971
Plasma Protein Binding (PPB):  43.14958190917969%
Volume Distribution (VD):  0.37
Pgp-substrate:  52.39229965209961%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.33
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.278
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.814
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.19
CYP3A4-inhibitor:  0.01
CYP3A4-substrate:  0.069

ADMET: Excretion

Clearance (CL):  6.575
Half-life (T1/2):  0.81

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.101
Drug-inuced Liver Injury (DILI):  0.056
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.199
Maximum Recommended Daily Dose:  0.01
Skin Sensitization:  0.179
Carcinogencity:  0.047
Eye Corrosion:  0.985
Eye Irritation:  0.994
Respiratory Toxicity:  0.199

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

  Natural Product: NPC122768

Natural Product ID:  NPC122768
Common Name*:   (R)-2-Methylbutanoate
IUPAC Name:   (2R)-2-methylbutanoic acid
Synonyms:   (R)-2-Methylbutanoate
Standard InCHIKey:  WLAMNBDJUVNPJU-SCSAIBSYSA-N
Standard InCHI:  InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m1/s1
SMILES:  CC[C@@H](C)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1162483
PubChem CID:   6950479
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000262] Fatty acids and conjugates
          • [CHEMONTID:0000338] Branched fatty acids
            • [CHEMONTID:0003544] Methyl-branched fatty acids

*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
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. root n.a. DOI[10.1007/s11418-007-0221-0]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/C39730000707]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota n.a. kernel n.a. PMID[10670815]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO25769 Heterotheca inuloides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[11473412]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[12502328]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[15730255]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota n.a. root n.a. PMID[15730255]
NPO6978 Boronella koniambiensis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[16038554]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. fruit n.a. PMID[16417304]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[16562834]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO26834 Eutypella scoparia Species Diatrypaceae Eukaryota n.a. n.a. n.a. PMID[16724861]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[17157006]
NPO651 Aconitum vilmorinianum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[17226159]
NPO13952 Streptomyces lavendulae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17237222]
NPO26211 Knightia excelsa Species Proteaceae Eukaryota n.a. n.a. n.a. PMID[17315967]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota Fruits Malatya Fruit Research Institute between the first and third weeks of 2005-Jul. PMID[18038980]
NPO4083 Brevibacillus laterosporus Species Paenibacillaceae Bacteria n.a. n.a. n.a. PMID[18044840]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18491868]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18611049]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18768384]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[19217780]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO26507 Galenia africana Species Aizoaceae Eukaryota leaf n.a. n.a. PMID[20035557]
NPO26654 Penicillium citreonigrum Species Aspergillaceae Eukaryota n.a. atlantic-forest-soil n.a. PMID[20450206]
NPO26834 Eutypella scoparia Species Diatrypaceae Eukaryota n.a. n.a. n.a. PMID[21302965]
NPO15884 Dodonaea polyandra Species Sapindaceae Eukaryota n.a. leaf n.a. PMID[21381684]
NPO15884 Dodonaea polyandra Species Sapindaceae Eukaryota n.a. stem n.a. PMID[21381684]
NPO15884 Dodonaea polyandra Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[21381684]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[21912858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[22111577]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. flower n.a. PMID[22166201]
NPO13952 Streptomyces lavendulae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22187429]
NPO651 Aconitum vilmorinianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[23784883]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[24155209]
NPO15884 Dodonaea polyandra Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[24400858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[24948953]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[24959987]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[25302569]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[25564559]
NPO25769 Heterotheca inuloides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26566007]
NPO10899 Ophioparma ventosa Species Ophioparmaceae Eukaryota n.a. n.a. n.a. PMID[26934105]
NPO7718 Peucedanum palustre Species Apiaceae Eukaryota n.a. root n.a. PMID[27133212]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO26451 Ophiocoma scolopendrina Species Ophiocomidae Eukaryota n.a. n.a. n.a. PMID[27684202]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[3373224]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7288445]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[7775984]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota Fruits n.a. Database[FooDB]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7718 Peucedanum palustre Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16307 Murraya kwangsiensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14111 Maytenus serrata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26134 Epimedium davidii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26699 Leonurus glaucescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16307 Murraya kwangsiensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7718 Peucedanum palustre Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14111 Maytenus serrata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5482 Gymnanthemum amygdalinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26349 Frullania tamarisci Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26134 Epimedium davidii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22505 Bombax ceiba Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25972 Eupolyphaga sinensis Species Corydiidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13427 Erinaceus europaeus Species Erinaceidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7718 Peucedanum palustre Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16307 Murraya kwangsiensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14111 Maytenus serrata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11421 Arnebia euchroma Species Boraginaceae 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]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26134 Epimedium davidii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26256 Zanthoxylum chiriquinum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26161 Globba malaccensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7718 Peucedanum palustre Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16109 Actinidia kolomikta Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25995 Laurencia distichophylla Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26023 Angelica tarokoensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO651 Aconitum vilmorinianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13952 Streptomyces lavendulae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25949 Streptomyces griseovariabilis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5750 Monomorium floricola Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4795 Prunus armeniaca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26950 Maba buxifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14747 Usnea florida Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26654 Penicillium citreonigrum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12547 Viburnum chingii Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10899 Ophioparma ventosa Species Ophioparmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16311 Rusavskia elegans Species Teloschistaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2898 Quercus sessiliflora Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22056.1 Streptomyces fervens Subspecies Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26451 Ophiocoma scolopendrina Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16307 Murraya kwangsiensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13740 Aconitum kamtschaticum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26319 Solanum acaule Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22053 Vepris pilosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13582 Leucopaxillus giganteus Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15312 Coelogorgia palmosa Species Coelogorgiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15679 Amyris marshii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15884 Dodonaea polyandra Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25792 Delphinium andersoni Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12951 Talaromyces coalescens Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11644 Prosopis ruscifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15570 Plectranthus mollis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7077 Canarium strictum Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26184 Diphasia angolensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13427 Erinaceus europaeus Species Erinaceidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14604 Dipteronia dyeriana Species Aceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16625 Phalaenopsis aphrodite Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26806 Nidula candida Species Nidulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7792 Coreopsis grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22505 Bombax ceiba Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4083 Brevibacillus laterosporus Species Paenibacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2607 Ophiorrhiza blumeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14442 Gouania microcarpa Species Gobiesocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26834 Eutypella scoparia Species Diatrypaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7447 Nemalion vermiculare Species Liagoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11376 Schistostephium rotundifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11421 Arnebia euchroma Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26607 Colobocentrotus atratus Species Echinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26052 Swertia delavayi Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25972 Eupolyphaga sinensis Species Corydiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12470 Brachyspira hyodysenteriae Species Brachyspiraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26406 Saussurea carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26287 Spodoptera eridania Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25739 Erysimum odoratum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16541 Veratrum stenophyllum Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9386 Ectropis bicolor Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14111 Maytenus serrata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14914 Esox saurus Species Esocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26584 Gnidia lamprantha Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15178 Psychotria bahiensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26699 Leonurus glaucescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25923 Vismia jefensis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26507 Galenia africana Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20297 Arnebia guttata Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26561 Micromeria pineolens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10452 Odontites rubra Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1723 Sideritis syriaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26624 Ilex amara Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11962 Garcinia macrophylla Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26349 Frullania tamarisci Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11776 Lithospermum erythrorhizon Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8671 Physalis solanaceus Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25896 Bragantia wallichii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12457 Siphocampylus verticillatus Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26900 Vallota purpurea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26211 Knightia excelsa Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5482 Gymnanthemum amygdalinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6978 Boronella koniambiensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26374 Alangium premnifolium Species Cornaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15434 Rhodomicrobium vannielii Species Hyphomicrobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13273 Maytenus loeseneri Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3697 Ongokea klaineana Species Aptandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15159 Podocarpus salignus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25769 Heterotheca inuloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT662 Individual Protein Solute carrier family 22 member 20 Mus musculus Ki = 40738.03 nM PMID[517435]
NPT661 Individual Protein Solute carrier family 22 member 6 Mus musculus Ki = 912010.84 nM PMID[517435]
NPT2 Others Unspecified Ratio pKi = 1.35 n.a. PMID[517435]

☑ 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 NPC122768 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 NPC61066
1.0 High Similarity NPC151140
1.0 High Similarity NPC104195
0.931 High Similarity NPC280532
0.8889 High Similarity NPC149209
0.8889 High Similarity NPC230726
0.871 High Similarity NPC307027
0.8438 Intermediate Similarity NPC316685
0.8214 Intermediate Similarity NPC314668
0.8 Intermediate Similarity NPC174368
0.7941 Intermediate Similarity NPC252843
0.7742 Intermediate Similarity NPC21374
0.7714 Intermediate Similarity NPC38930
0.7714 Intermediate Similarity NPC325454
0.75 Intermediate Similarity NPC3531
0.75 Intermediate Similarity NPC222792
0.75 Intermediate Similarity NPC316217
0.7419 Intermediate Similarity NPC292641
0.7407 Intermediate Similarity NPC181153
0.7273 Intermediate Similarity NPC168714
0.7273 Intermediate Similarity NPC41007
0.7273 Intermediate Similarity NPC35371
0.7273 Intermediate Similarity NPC175342
0.7273 Intermediate Similarity NPC178643
0.7241 Intermediate Similarity NPC28246
0.7188 Intermediate Similarity NPC241404
0.7188 Intermediate Similarity NPC320981
0.7188 Intermediate Similarity NPC198126
0.7105 Intermediate Similarity NPC325452
0.7105 Intermediate Similarity NPC248763
0.7097 Intermediate Similarity NPC281943
0.7097 Intermediate Similarity NPC236709
0.7097 Intermediate Similarity NPC317739
0.7059 Intermediate Similarity NPC7814
0.7059 Intermediate Similarity NPC127142
0.7 Intermediate Similarity NPC211250
0.697 Remote Similarity NPC212144
0.697 Remote Similarity NPC328569
0.6857 Remote Similarity NPC250870
0.6857 Remote Similarity NPC191084
0.6857 Remote Similarity NPC168052
0.6842 Remote Similarity NPC240109
0.6774 Remote Similarity NPC143211
0.6765 Remote Similarity NPC18224
0.6765 Remote Similarity NPC328710
0.6765 Remote Similarity NPC125575
0.6765 Remote Similarity NPC94196
0.675 Remote Similarity NPC132307
0.675 Remote Similarity NPC325097
0.675 Remote Similarity NPC126925
0.675 Remote Similarity NPC319680
0.6667 Remote Similarity NPC155263
0.6667 Remote Similarity NPC5505
0.6585 Remote Similarity NPC55023
0.6552 Remote Similarity NPC8187
0.6552 Remote Similarity NPC203105
0.65 Remote Similarity NPC310220
0.6486 Remote Similarity NPC109026
0.6486 Remote Similarity NPC206924
0.6486 Remote Similarity NPC14608
0.6486 Remote Similarity NPC158179
0.6452 Remote Similarity NPC201132
0.6452 Remote Similarity NPC166804
0.6452 Remote Similarity NPC286233
0.6429 Remote Similarity NPC314679
0.6389 Remote Similarity NPC317203
0.6364 Remote Similarity NPC127696
0.6364 Remote Similarity NPC180423
0.6333 Remote Similarity NPC23071
0.6333 Remote Similarity NPC256186
0.6316 Remote Similarity NPC73245
0.6296 Remote Similarity NPC68873
0.6286 Remote Similarity NPC14778
0.6279 Remote Similarity NPC21844
0.6216 Remote Similarity NPC134782
0.6216 Remote Similarity NPC9294
0.6207 Remote Similarity NPC83723
0.6176 Remote Similarity NPC302611
0.6176 Remote Similarity NPC16947
0.6154 Remote Similarity NPC301585
0.6154 Remote Similarity NPC329545
0.6154 Remote Similarity NPC14227
0.6154 Remote Similarity NPC301696
0.6154 Remote Similarity NPC261080
0.6154 Remote Similarity NPC154186
0.6154 Remote Similarity NPC113928
0.6154 Remote Similarity NPC201844
0.6154 Remote Similarity NPC279026
0.6136 Remote Similarity NPC324793
0.6136 Remote Similarity NPC477878
0.6129 Remote Similarity NPC227197
0.6129 Remote Similarity NPC32280
0.6129 Remote Similarity NPC307594
0.6129 Remote Similarity NPC289974
0.6129 Remote Similarity NPC304927
0.6129 Remote Similarity NPC41485
0.6129 Remote Similarity NPC3693
0.6111 Remote Similarity NPC217161
0.6053 Remote Similarity NPC317945
0.6047 Remote Similarity NPC133771
0.6 Remote Similarity NPC84636
0.6 Remote Similarity NPC121517
0.6 Remote Similarity NPC245027
0.6 Remote Similarity NPC62045
0.6 Remote Similarity NPC226027
0.6 Remote Similarity NPC12904
0.6 Remote Similarity NPC174246
0.6 Remote Similarity NPC168375
0.6 Remote Similarity NPC43204
0.6 Remote Similarity NPC328378
0.6 Remote Similarity NPC326992
0.6 Remote Similarity NPC162620
0.6 Remote Similarity NPC66043
0.5946 Remote Similarity NPC155872
0.5938 Remote Similarity NPC259649
0.5938 Remote Similarity NPC3343
0.5897 Remote Similarity NPC18188
0.5897 Remote Similarity NPC268826
0.5882 Remote Similarity NPC248139
0.5862 Remote Similarity NPC106054
0.5862 Remote Similarity NPC260610
0.5854 Remote Similarity NPC216630
0.5854 Remote Similarity NPC163746
0.5854 Remote Similarity NPC171736
0.5854 Remote Similarity NPC149184
0.5854 Remote Similarity NPC196924
0.5854 Remote Similarity NPC103286
0.5854 Remote Similarity NPC209970
0.5854 Remote Similarity NPC307783
0.5833 Remote Similarity NPC286695
0.5833 Remote Similarity NPC108238
0.5806 Remote Similarity NPC87529
0.5806 Remote Similarity NPC91093
0.5806 Remote Similarity NPC110107
0.5789 Remote Similarity NPC1037
0.5758 Remote Similarity NPC39869
0.5758 Remote Similarity NPC283626
0.5758 Remote Similarity NPC100997
0.5758 Remote Similarity NPC276332
0.5758 Remote Similarity NPC248233
0.5758 Remote Similarity NPC320704
0.575 Remote Similarity NPC81263
0.575 Remote Similarity NPC183424
0.575 Remote Similarity NPC327250
0.575 Remote Similarity NPC294085
0.575 Remote Similarity NPC118968
0.575 Remote Similarity NPC214610
0.5745 Remote Similarity NPC48162
0.5745 Remote Similarity NPC322946
0.5714 Remote Similarity NPC167986
0.5714 Remote Similarity NPC283245
0.5714 Remote Similarity NPC289686
0.5714 Remote Similarity NPC71317
0.5714 Remote Similarity NPC129972
0.5714 Remote Similarity NPC67462
0.5714 Remote Similarity NPC301528
0.5714 Remote Similarity NPC291186
0.5676 Remote Similarity NPC154396
0.5676 Remote Similarity NPC57499
0.5667 Remote Similarity NPC222945
0.5667 Remote Similarity NPC88839
0.5641 Remote Similarity NPC321569
0.5625 Remote Similarity NPC190797

  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 NPC122768 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
0.7931 Intermediate Similarity NPD8990 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9450 Approved
0.75 Intermediate Similarity NPD77 Approved
0.7407 Intermediate Similarity NPD8616 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD8615 Phase 2
0.7407 Intermediate Similarity NPD8201 Phase 2
0.7297 Intermediate Similarity NPD9635 Discontinued
0.7188 Intermediate Similarity NPD8590 Approved
0.7188 Intermediate Similarity NPD8618 Approved
0.7097 Intermediate Similarity NPD8594 Approved
0.7097 Intermediate Similarity NPD8593 Approved
0.7059 Intermediate Similarity NPD8857 Approved
0.6875 Remote Similarity NPD8617 Approved
0.6875 Remote Similarity NPD8619 Approved
0.6857 Remote Similarity NPD9447 Approved
0.675 Remote Similarity NPD8798 Approved
0.6486 Remote Similarity NPD9449 Clinical (unspecified phase)
0.6452 Remote Similarity NPD8189 Approved
0.6429 Remote Similarity NPD634 Phase 3
0.6341 Remote Similarity NPD8975 Clinical (unspecified phase)
0.6296 Remote Similarity NPD7364 Approved
0.6296 Remote Similarity NPD8200 Phase 2
0.625 Remote Similarity NPD106 Approved
0.625 Remote Similarity NPD9116 Phase 1
0.619 Remote Similarity NPD8974 Clinical (unspecified phase)
0.6154 Remote Similarity NPD9448 Phase 2
0.6154 Remote Similarity NPD633 Phase 3
0.6129 Remote Similarity NPD8591 Approved
0.6129 Remote Similarity NPD8592 Approved
0.6047 Remote Similarity NPD8801 Approved
0.6 Remote Similarity NPD9017 Approved
0.6 Remote Similarity NPD9018 Approved
0.5952 Remote Similarity NPD9411 Phase 1
0.5946 Remote Similarity NPD8596 Approved
0.5897 Remote Similarity NPD8623 Phase 1
0.5882 Remote Similarity NPD62 Approved
0.5854 Remote Similarity NPD2270 Approved
0.5814 Remote Similarity NPD9658 Clinical (unspecified phase)
0.5789 Remote Similarity NPD8597 Approved
0.5778 Remote Similarity NPD2266 Phase 2
0.575 Remote Similarity NPD9655 Approved
0.5745 Remote Similarity NPD9441 Phase 2
0.5714 Remote Similarity NPD8804 Approved
0.5714 Remote Similarity NPD8805 Approved
0.5676 Remote Similarity NPD900 Approved
0.5652 Remote Similarity NPD8947 Approved
0.5652 Remote Similarity NPD8946 Approved
0.5625 Remote Similarity NPD3186 Phase 1

  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