Structure

Physi-Chem Properties

Molecular Weight:  136.13
Volume:  161.767
LogP:  4.138
LogD:  3.703
LogS:  -4.597
# Rotatable Bonds:  0
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.449
Synthetic Accessibility Score:  3.659
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.373
MDCK Permeability:  1.9748413251363672e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.153
30% Bioavailability (F30%):  0.226

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.687
Plasma Protein Binding (PPB):  93.78605651855469%
Volume Distribution (VD):  3.838
Pgp-substrate:  7.778956890106201%

ADMET: Metabolism

CYP1A2-inhibitor:  0.729
CYP1A2-substrate:  0.516
CYP2C19-inhibitor:  0.335
CYP2C19-substrate:  0.893
CYP2C9-inhibitor:  0.364
CYP2C9-substrate:  0.853
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.466
CYP3A4-inhibitor:  0.044
CYP3A4-substrate:  0.283

ADMET: Excretion

Clearance (CL):  9.034
Half-life (T1/2):  0.103

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.334
Drug-inuced Liver Injury (DILI):  0.198
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.1
Maximum Recommended Daily Dose:  0.316
Skin Sensitization:  0.086
Carcinogencity:  0.048
Eye Corrosion:  0.305
Eye Irritation:  0.641
Respiratory Toxicity:  0.839

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

  Natural Product: NPC248411

Natural Product ID:  NPC248411
Common Name*:   2-Carene
IUPAC Name:   4,7,7-trimethylbicyclo[4.1.0]hept-4-ene
Synonyms:  
Standard InCHIKey:  IBVJWOMJGCHRRW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6,8-9H,4-5H2,1-3H3
SMILES:  CC1=CC2C(CC1)C2(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2286984
PubChem CID:   79044
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001564] Bicyclic 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
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. stem n.a. DOI[10.1007/s11418-006-0112-9]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. flower n.a. DOI[10.1007/s11418-006-0112-9]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[11374978]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. leaf n.a. PMID[15388977]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15679317]
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]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. stem n.a. PMID[17202689]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. root n.a. PMID[17997069]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. pericarp n.a. PMID[20628994]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. bark n.a. PMID[21875098]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23755850]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[24155209]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[24175626]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[24868863]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[24959987]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[25089845]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[25302569]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25538068]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27400088]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[28682072]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[29099182]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Twigs n.a. n.a. PMID[29883114]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota Bark 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]
NPO30125 0topterygium forbesii n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8367 Fructus schiandrae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12322 Amomum krervanh Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22033 Cnidium officinale Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8367 Fructus schiandrae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22258 Chrysanthemum indicum Species Asteraceae 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]
NPO18951 Ligusticum sinense Species Apiaceae 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]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae 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]
NPO30125 0topterygium forbesii n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31311 Citrus reticulate Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31073 Ligusticum chuanxiong Species Apiaceae 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]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae 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]
NPO22033 Cnidium officinale Species Apiaceae 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]
NPO18951 Ligusticum sinense Species Apiaceae 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]
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24644 Hansenia forbesii 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]
NPO12322 Amomum krervanh Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29010 Amomum compactum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2953 Ostericum grosseserratum Species Apiaceae 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]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12322 Amomum krervanh Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11438 Angelica gigas Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2953 Ostericum grosseserratum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15462 Angelica sinensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8698 Zanthoxylum schinifolium Species Rutaceae 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
NPT780 Organism Sitophilus zeamais Sitophilus zeamais LD50 = 3.55 mg.kg-1 PMID[456467]
NPT780 Organism Sitophilus zeamais Sitophilus zeamais LC50 = 14.02 ug.mL-1 PMID[456467]

☑ 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 NPC248411 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9762 High Similarity NPC296337
0.8837 High Similarity NPC86538
0.8537 High Similarity NPC229262
0.8537 High Similarity NPC297643
0.8537 High Similarity NPC139717
0.8444 Intermediate Similarity NPC86683
0.8444 Intermediate Similarity NPC241784
0.8444 Intermediate Similarity NPC114239
0.8444 Intermediate Similarity NPC13991
0.8298 Intermediate Similarity NPC17518
0.8293 Intermediate Similarity NPC34764
0.8293 Intermediate Similarity NPC190810
0.8293 Intermediate Similarity NPC76145
0.8222 Intermediate Similarity NPC202189
0.8182 Intermediate Similarity NPC177470
0.8085 Intermediate Similarity NPC124851
0.8 Intermediate Similarity NPC60556
0.8 Intermediate Similarity NPC109813
0.8 Intermediate Similarity NPC192529
0.7955 Intermediate Similarity NPC144023
0.7917 Intermediate Similarity NPC22765
0.7778 Intermediate Similarity NPC190232
0.7778 Intermediate Similarity NPC105246
0.7755 Intermediate Similarity NPC200129
0.7727 Intermediate Similarity NPC183670
0.7727 Intermediate Similarity NPC246165
0.7674 Intermediate Similarity NPC239039
0.766 Intermediate Similarity NPC49088
0.75 Intermediate Similarity NPC323445
0.7391 Intermediate Similarity NPC193180
0.7391 Intermediate Similarity NPC473912
0.7358 Intermediate Similarity NPC469770
0.7333 Intermediate Similarity NPC227632
0.7333 Intermediate Similarity NPC78551
0.7333 Intermediate Similarity NPC62086
0.7317 Intermediate Similarity NPC213749
0.7273 Intermediate Similarity NPC48638
0.7273 Intermediate Similarity NPC45727
0.7234 Intermediate Similarity NPC90803
0.7234 Intermediate Similarity NPC23145
0.7234 Intermediate Similarity NPC90506
0.7209 Intermediate Similarity NPC92224
0.72 Intermediate Similarity NPC17810
0.7174 Intermediate Similarity NPC218918
0.7174 Intermediate Similarity NPC120926
0.7174 Intermediate Similarity NPC103290
0.7115 Intermediate Similarity NPC181255
0.7115 Intermediate Similarity NPC306195
0.7115 Intermediate Similarity NPC473728
0.7115 Intermediate Similarity NPC157781
0.7115 Intermediate Similarity NPC179169
0.7115 Intermediate Similarity NPC35519
0.7091 Intermediate Similarity NPC474528
0.7091 Intermediate Similarity NPC474415
0.7091 Intermediate Similarity NPC475696
0.7073 Intermediate Similarity NPC3649
0.7037 Intermediate Similarity NPC123194
0.7037 Intermediate Similarity NPC470893
0.7 Intermediate Similarity NPC178644
0.6981 Remote Similarity NPC476679
0.6964 Remote Similarity NPC469769
0.6949 Remote Similarity NPC285371
0.6923 Remote Similarity NPC214584
0.6923 Remote Similarity NPC26906
0.6889 Remote Similarity NPC266298
0.6852 Remote Similarity NPC5626
0.6842 Remote Similarity NPC474455
0.6842 Remote Similarity NPC474420
0.6842 Remote Similarity NPC475716
0.6842 Remote Similarity NPC474454
0.6818 Remote Similarity NPC282119
0.6792 Remote Similarity NPC177112
0.6792 Remote Similarity NPC71506
0.6786 Remote Similarity NPC474457
0.6667 Remote Similarity NPC66577
0.6667 Remote Similarity NPC268564
0.6667 Remote Similarity NPC23117
0.6667 Remote Similarity NPC206088
0.6667 Remote Similarity NPC14002
0.661 Remote Similarity NPC469728
0.6604 Remote Similarity NPC244038
0.6557 Remote Similarity NPC470329
0.6538 Remote Similarity NPC62755
0.6531 Remote Similarity NPC51762
0.6531 Remote Similarity NPC227670
0.6531 Remote Similarity NPC141777
0.6531 Remote Similarity NPC474118
0.6531 Remote Similarity NPC166362
0.65 Remote Similarity NPC283247
0.65 Remote Similarity NPC165695
0.6491 Remote Similarity NPC470369
0.6491 Remote Similarity NPC11130
0.6491 Remote Similarity NPC470370
0.6491 Remote Similarity NPC115385
0.6441 Remote Similarity NPC127582
0.6441 Remote Similarity NPC176621
0.6441 Remote Similarity NPC135648
0.6441 Remote Similarity NPC311809
0.6393 Remote Similarity NPC469662
0.6393 Remote Similarity NPC475124
0.6393 Remote Similarity NPC6697
0.6393 Remote Similarity NPC475704
0.6379 Remote Similarity NPC170799
0.6379 Remote Similarity NPC308108
0.6379 Remote Similarity NPC60772
0.6379 Remote Similarity NPC56905
0.6379 Remote Similarity NPC27610
0.6364 Remote Similarity NPC295777
0.6364 Remote Similarity NPC165755
0.6364 Remote Similarity NPC69898
0.6346 Remote Similarity NPC91962
0.6333 Remote Similarity NPC219621
0.6333 Remote Similarity NPC60565
0.6333 Remote Similarity NPC213152
0.6316 Remote Similarity NPC55412
0.6316 Remote Similarity NPC179024
0.6316 Remote Similarity NPC141699
0.6316 Remote Similarity NPC249645
0.6296 Remote Similarity NPC27438
0.629 Remote Similarity NPC251118
0.6279 Remote Similarity NPC471327
0.6279 Remote Similarity NPC100879
0.6275 Remote Similarity NPC229403
0.6271 Remote Similarity NPC309825
0.6271 Remote Similarity NPC276764
0.6271 Remote Similarity NPC472304
0.623 Remote Similarity NPC474086
0.623 Remote Similarity NPC197238
0.623 Remote Similarity NPC202118
0.6226 Remote Similarity NPC106990
0.6212 Remote Similarity NPC304983
0.6207 Remote Similarity NPC55004
0.6207 Remote Similarity NPC208749
0.6207 Remote Similarity NPC192427
0.6207 Remote Similarity NPC321568
0.6207 Remote Similarity NPC49575
0.6207 Remote Similarity NPC267626
0.6207 Remote Similarity NPC165808
0.6207 Remote Similarity NPC281986
0.6207 Remote Similarity NPC230823
0.6207 Remote Similarity NPC22019
0.619 Remote Similarity NPC222366
0.619 Remote Similarity NPC135650
0.619 Remote Similarity NPC476039
0.619 Remote Similarity NPC176171
0.619 Remote Similarity NPC259156
0.619 Remote Similarity NPC286669
0.619 Remote Similarity NPC92327
0.619 Remote Similarity NPC242945
0.619 Remote Similarity NPC279434
0.6182 Remote Similarity NPC294358
0.6182 Remote Similarity NPC40417
0.6154 Remote Similarity NPC159420
0.614 Remote Similarity NPC298299
0.614 Remote Similarity NPC200258
0.6129 Remote Similarity NPC290367
0.6129 Remote Similarity NPC107540
0.6129 Remote Similarity NPC212210
0.6122 Remote Similarity NPC473614
0.6111 Remote Similarity NPC32351
0.6111 Remote Similarity NPC58970
0.6111 Remote Similarity NPC228776
0.6111 Remote Similarity NPC329773
0.6111 Remote Similarity NPC182102
0.6111 Remote Similarity NPC116906
0.6111 Remote Similarity NPC26960
0.6111 Remote Similarity NPC476681
0.6111 Remote Similarity NPC176819
0.6111 Remote Similarity NPC163984
0.6102 Remote Similarity NPC94991
0.6102 Remote Similarity NPC266295
0.6102 Remote Similarity NPC30215
0.6102 Remote Similarity NPC472830
0.6102 Remote Similarity NPC311852
0.6098 Remote Similarity NPC10183
0.6094 Remote Similarity NPC171225
0.6094 Remote Similarity NPC290350
0.6094 Remote Similarity NPC176107
0.6094 Remote Similarity NPC193770
0.6094 Remote Similarity NPC4370
0.6094 Remote Similarity NPC114651
0.6094 Remote Similarity NPC197805
0.6071 Remote Similarity NPC127944
0.6071 Remote Similarity NPC474416
0.6066 Remote Similarity NPC79576
0.6066 Remote Similarity NPC282694
0.6066 Remote Similarity NPC194208
0.6061 Remote Similarity NPC214770
0.6061 Remote Similarity NPC151045
0.6061 Remote Similarity NPC477856
0.6061 Remote Similarity NPC246722
0.6034 Remote Similarity NPC39068
0.6032 Remote Similarity NPC163678
0.6032 Remote Similarity NPC61503
0.6 Remote Similarity NPC236623
0.6 Remote Similarity NPC142754
0.6 Remote Similarity NPC5698
0.6 Remote Similarity NPC188292
0.6 Remote Similarity NPC96484
0.6 Remote Similarity NPC472827

  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 NPC248411 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
0.8293 Intermediate Similarity NPD319 Phase 1
0.7778 Intermediate Similarity NPD1799 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD8262 Approved
0.6379 Remote Similarity NPD287 Approved
0.6316 Remote Similarity NPD4219 Approved
0.6 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5909 Remote Similarity NPD4137 Phase 3
0.5862 Remote Similarity NPD342 Phase 1
0.5821 Remote Similarity NPD6939 Phase 2
0.5821 Remote Similarity NPD6938 Clinical (unspecified phase)
0.5821 Remote Similarity NPD4747 Approved
0.5821 Remote Similarity NPD4691 Approved
0.5806 Remote Similarity NPD4194 Approved
0.5806 Remote Similarity NPD4191 Approved
0.5806 Remote Similarity NPD4192 Approved
0.5806 Remote Similarity NPD368 Approved
0.5806 Remote Similarity NPD4193 Approved
0.5735 Remote Similarity NPD4243 Approved
0.5625 Remote Similarity NPD5325 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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