Structure

Physi-Chem Properties

Molecular Weight:  154.14
Volume:  173.194
LogP:  2.864
LogD:  2.973
LogS:  -2.156
# Rotatable Bonds:  0
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.567
Synthetic Accessibility Score:  4.639
Fsp3:  1.0
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:  -4.541
MDCK Permeability:  2.724582009250298e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.061
30% Bioavailability (F30%):  0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.393
Plasma Protein Binding (PPB):  63.50156021118164%
Volume Distribution (VD):  0.984
Pgp-substrate:  41.93745040893555%

ADMET: Metabolism

CYP1A2-inhibitor:  0.249
CYP1A2-substrate:  0.431
CYP2C19-inhibitor:  0.135
CYP2C19-substrate:  0.825
CYP2C9-inhibitor:  0.168
CYP2C9-substrate:  0.607
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.667
CYP3A4-inhibitor:  0.029
CYP3A4-substrate:  0.214

ADMET: Excretion

Clearance (CL):  7.23
Half-life (T1/2):  0.534

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.129
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.113
Rat Oral Acute Toxicity:  0.959
Maximum Recommended Daily Dose:  0.966
Skin Sensitization:  0.579
Carcinogencity:  0.055
Eye Corrosion:  0.917
Eye Irritation:  0.981
Respiratory Toxicity:  0.952

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Similar NPs/Drugs  

  Natural Product: NPC29976

Natural Product ID:  NPC29976
Common Name*:   (1S,3R,4R)-2,2,4-Trimethylbicyclo[2.2.1]Heptan-3-Ol
IUPAC Name:   (1S,3R,4R)-2,2,4-trimethylbicyclo[2.2.1]heptan-3-ol
Synonyms:  
Standard InCHIKey:  IAIHUHQCLTYTSF-OYNCUSHFSA-N
Standard InCHI:  InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1
SMILES:  CC1(C)[C@H]2CC[C@](C)(C2)[C@H]1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3188732
PubChem CID:   6997371
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. 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]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. leaf n.a. DOI[10.1007/s11418-006-0112-9]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. stem n.a. DOI[10.1016/0031-9422(86)88033-5]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/0031-9422(86)88033-5]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota whole plant n.a. n.a. DOI[10.1016/j.tetlet.2016.12.029]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(00)94055-X]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. flower n.a. DOI[10.3390/70200245]
NPO13539 Thuja occidentalis Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[11000026]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota Leaves and branches Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota leaves Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota seeds n.a. n.a. PMID[17998162]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[18177011]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[19271742]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. PMID[1955885]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[20590154]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. fruit n.a. PMID[20879744]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. seed n.a. PMID[21049973]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. stem n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[21226514]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO27751 Pinus radiata Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[23131896]
NPO7591 Cedrus deodara Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[23387901]
NPO24816 Anaphalis contorta Species Asteraceae Eukaryota n.a. flower n.a. PMID[23513735]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[23701597]
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]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24617303]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[25819096]
NPO6316 Abies balsamea Species Pinaceae Eukaryota Oleoresin n.a. n.a. PMID[26592897]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. PMID[27419473]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. PMID[6387056]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8064299]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO6316 Abies balsamea Species Pinaceae Eukaryota n.a. whole plant n.a. Database[Article]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Aril n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24816 Anaphalis contorta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6316 Abies balsamea Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13539 Thuja occidentalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30036 Chenopodium botrys Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27751 Pinus radiata Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30851 Magnolia liliflora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7591 Cedrus deodara Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31384 Thuja orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO13730 Magnolia liliiflora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22014 Dysphania botrys Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2048 Rhizoma curcumae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO6316 Abies balsamea Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27751 Pinus radiata Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24816 Anaphalis contorta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28295 Foeniculum vulgare 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]
NPO7591 Cedrus deodara Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26589 Artemisia annua L. Strain Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13539 Thuja occidentalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7591 Cedrus deodara Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28256 Platycladus orientalis Species Cupressaceae 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]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17494 Prunella vulgaris Species Lamiaceae 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]
NPO30851 Magnolia liliflora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31384 Thuja orientalis Species Cupressaceae 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]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO28295 Foeniculum vulgare Species Apiaceae 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]
NPO7929 Curcuma zedoaria Species Zingiberaceae 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]
NPO2978 Croton tiglium Species Euphorbiaceae 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]
NPO5241 Myristica fragrans Species Myristicaceae 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]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27751 Pinus radiata Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2978 Croton tiglium Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24816 Anaphalis contorta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22014 Dysphania botrys Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13539 Thuja occidentalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7698 Elettaria cardamomum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7591 Cedrus deodara Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13730 Magnolia liliiflora Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26589 Artemisia annua L. Strain 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
NPT2 Others Unspecified Potency n.a. 201.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 31731.6 nM PubChem BioAssay data set

☑ 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 NPC29976 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 NPC150713
0.9623 High Similarity NPC89069
0.9623 High Similarity NPC166894
0.9623 High Similarity NPC283655
0.9623 High Similarity NPC277917
0.9623 High Similarity NPC178223
0.8197 Intermediate Similarity NPC249078
0.8197 Intermediate Similarity NPC236099
0.8197 Intermediate Similarity NPC209686
0.8103 Intermediate Similarity NPC3025
0.807 Intermediate Similarity NPC202146
0.807 Intermediate Similarity NPC32222
0.8033 Intermediate Similarity NPC83088
0.8033 Intermediate Similarity NPC95804
0.8033 Intermediate Similarity NPC185547
0.7846 Intermediate Similarity NPC474756
0.7812 Intermediate Similarity NPC44122
0.7778 Intermediate Similarity NPC118937
0.7778 Intermediate Similarity NPC159654
0.7778 Intermediate Similarity NPC281540
0.7778 Intermediate Similarity NPC167995
0.7759 Intermediate Similarity NPC53209
0.7742 Intermediate Similarity NPC148174
0.7742 Intermediate Similarity NPC71460
0.7742 Intermediate Similarity NPC218585
0.7727 Intermediate Similarity NPC477820
0.7705 Intermediate Similarity NPC230070
0.7705 Intermediate Similarity NPC9880
0.7705 Intermediate Similarity NPC87828
0.7692 Intermediate Similarity NPC74885
0.7692 Intermediate Similarity NPC308522
0.7692 Intermediate Similarity NPC63190
0.7681 Intermediate Similarity NPC131584
0.7681 Intermediate Similarity NPC313185
0.7681 Intermediate Similarity NPC139765
0.7667 Intermediate Similarity NPC291147
0.7656 Intermediate Similarity NPC473276
0.7656 Intermediate Similarity NPC41577
0.7656 Intermediate Similarity NPC474380
0.7619 Intermediate Similarity NPC114891
0.7612 Intermediate Similarity NPC251201
0.7612 Intermediate Similarity NPC232925
0.7612 Intermediate Similarity NPC63588
0.7581 Intermediate Similarity NPC66145
0.7538 Intermediate Similarity NPC142712
0.75 Intermediate Similarity NPC69149
0.746 Intermediate Similarity NPC147524
0.7455 Intermediate Similarity NPC147343
0.7455 Intermediate Similarity NPC287550
0.7455 Intermediate Similarity NPC176309
0.7455 Intermediate Similarity NPC84030
0.7455 Intermediate Similarity NPC198540
0.7455 Intermediate Similarity NPC223468
0.7424 Intermediate Similarity NPC48079
0.7424 Intermediate Similarity NPC475884
0.7424 Intermediate Similarity NPC473230
0.7419 Intermediate Similarity NPC475968
0.7391 Intermediate Similarity NPC14352
0.7391 Intermediate Similarity NPC153719
0.7391 Intermediate Similarity NPC234527
0.7391 Intermediate Similarity NPC470610
0.7385 Intermediate Similarity NPC243469
0.7385 Intermediate Similarity NPC190827
0.7385 Intermediate Similarity NPC475943
0.7333 Intermediate Similarity NPC471269
0.7313 Intermediate Similarity NPC472741
0.7286 Intermediate Similarity NPC477508
0.7286 Intermediate Similarity NPC304499
0.7286 Intermediate Similarity NPC48795
0.7286 Intermediate Similarity NPC309178
0.7286 Intermediate Similarity NPC475458
0.726 Intermediate Similarity NPC329871
0.726 Intermediate Similarity NPC269333
0.7258 Intermediate Similarity NPC476735
0.7231 Intermediate Similarity NPC219940
0.7206 Intermediate Similarity NPC241085
0.7206 Intermediate Similarity NPC66407
0.7206 Intermediate Similarity NPC129829
0.7206 Intermediate Similarity NPC470830
0.7206 Intermediate Similarity NPC299948
0.7206 Intermediate Similarity NPC254037
0.7206 Intermediate Similarity NPC107919
0.7183 Intermediate Similarity NPC317242
0.7162 Intermediate Similarity NPC117137
0.7162 Intermediate Similarity NPC66766
0.7143 Intermediate Similarity NPC95958
0.7121 Intermediate Similarity NPC472946
0.7121 Intermediate Similarity NPC300442
0.7101 Intermediate Similarity NPC192192
0.7101 Intermediate Similarity NPC282454
0.7101 Intermediate Similarity NPC231945
0.7097 Intermediate Similarity NPC236588
0.7097 Intermediate Similarity NPC135438
0.7097 Intermediate Similarity NPC119425
0.7083 Intermediate Similarity NPC163597
0.7083 Intermediate Similarity NPC470145
0.7 Intermediate Similarity NPC131506
0.7 Intermediate Similarity NPC157777
0.7 Intermediate Similarity NPC111234
0.7 Intermediate Similarity NPC109457
0.7 Intermediate Similarity NPC478103
0.7 Intermediate Similarity NPC187471
0.7 Intermediate Similarity NPC252182
0.7 Intermediate Similarity NPC100586
0.7 Intermediate Similarity NPC470071
0.7 Intermediate Similarity NPC473279
0.7 Intermediate Similarity NPC195530
0.7 Intermediate Similarity NPC127094
0.7 Intermediate Similarity NPC1340
0.7 Intermediate Similarity NPC157422
0.6986 Remote Similarity NPC477227
0.6986 Remote Similarity NPC302578
0.6986 Remote Similarity NPC128951
0.6986 Remote Similarity NPC476233
0.6986 Remote Similarity NPC192046
0.6986 Remote Similarity NPC185915
0.6986 Remote Similarity NPC105208
0.6957 Remote Similarity NPC321732
0.6957 Remote Similarity NPC324607
0.6949 Remote Similarity NPC307022
0.6944 Remote Similarity NPC270306
0.6944 Remote Similarity NPC91387
0.6944 Remote Similarity NPC231680
0.6901 Remote Similarity NPC473238
0.6901 Remote Similarity NPC310766
0.6901 Remote Similarity NPC232112
0.6901 Remote Similarity NPC201373
0.6901 Remote Similarity NPC472341
0.6897 Remote Similarity NPC95969
0.6897 Remote Similarity NPC127997
0.6892 Remote Similarity NPC42853
0.6892 Remote Similarity NPC67657
0.6892 Remote Similarity NPC18857
0.6892 Remote Similarity NPC477819
0.6892 Remote Similarity NPC471045
0.6892 Remote Similarity NPC477817
0.6883 Remote Similarity NPC69953
0.6883 Remote Similarity NPC29342
0.6883 Remote Similarity NPC2572
0.6866 Remote Similarity NPC477009
0.6866 Remote Similarity NPC165069
0.6866 Remote Similarity NPC238352
0.6857 Remote Similarity NPC133873
0.6857 Remote Similarity NPC254845
0.6857 Remote Similarity NPC45296
0.6818 Remote Similarity NPC290791
0.6818 Remote Similarity NPC292419
0.6806 Remote Similarity NPC192638
0.6806 Remote Similarity NPC25511
0.6806 Remote Similarity NPC145552
0.6806 Remote Similarity NPC10476
0.6806 Remote Similarity NPC5046
0.6806 Remote Similarity NPC62657
0.6806 Remote Similarity NPC192501
0.6806 Remote Similarity NPC49168
0.6806 Remote Similarity NPC478130
0.6806 Remote Similarity NPC228994
0.6806 Remote Similarity NPC196358
0.6806 Remote Similarity NPC254509
0.68 Remote Similarity NPC287452
0.68 Remote Similarity NPC49627
0.68 Remote Similarity NPC1319
0.68 Remote Similarity NPC49599
0.6795 Remote Similarity NPC242016
0.6774 Remote Similarity NPC45387
0.6769 Remote Similarity NPC84218
0.6761 Remote Similarity NPC156277
0.6761 Remote Similarity NPC320549
0.6761 Remote Similarity NPC127283
0.6761 Remote Similarity NPC89310
0.6761 Remote Similarity NPC151018
0.6761 Remote Similarity NPC58057
0.6761 Remote Similarity NPC8004
0.6761 Remote Similarity NPC164045
0.6757 Remote Similarity NPC133596
0.6757 Remote Similarity NPC307336
0.6757 Remote Similarity NPC474574
0.6757 Remote Similarity NPC138502
0.6757 Remote Similarity NPC260301
0.6757 Remote Similarity NPC64081
0.6757 Remote Similarity NPC171658
0.6757 Remote Similarity NPC11907
0.6753 Remote Similarity NPC470611
0.6753 Remote Similarity NPC296734
0.6753 Remote Similarity NPC475388
0.6721 Remote Similarity NPC36002
0.6721 Remote Similarity NPC102336
0.6719 Remote Similarity NPC162685
0.6719 Remote Similarity NPC47663
0.6719 Remote Similarity NPC87296
0.6719 Remote Similarity NPC475515
0.6719 Remote Similarity NPC215671
0.6716 Remote Similarity NPC101128
0.6714 Remote Similarity NPC131892
0.6714 Remote Similarity NPC99264
0.6714 Remote Similarity NPC6120
0.6714 Remote Similarity NPC213178
0.6714 Remote Similarity NPC327728
0.6712 Remote Similarity NPC212879
0.6712 Remote Similarity NPC185536

  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 NPC29976 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
0.7455 Intermediate Similarity NPD385 Approved
0.7455 Intermediate Similarity NPD384 Approved
0.7353 Intermediate Similarity NPD4787 Phase 1
0.7213 Intermediate Similarity NPD586 Phase 1
0.7206 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3698 Phase 2
0.6866 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6857 Remote Similarity NPD4244 Approved
0.6857 Remote Similarity NPD4245 Approved
0.6761 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6761 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6714 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6714 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6711 Remote Similarity NPD6928 Phase 2
0.6622 Remote Similarity NPD6117 Approved
0.6575 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6533 Remote Similarity NPD6116 Phase 1
0.6494 Remote Similarity NPD4748 Discontinued
0.6486 Remote Similarity NPD3703 Phase 2
0.6447 Remote Similarity NPD6115 Approved
0.6447 Remote Similarity NPD6697 Approved
0.6447 Remote Similarity NPD6114 Approved
0.6447 Remote Similarity NPD6118 Approved
0.64 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6389 Remote Similarity NPD4789 Approved
0.6364 Remote Similarity NPD3198 Approved
0.6338 Remote Similarity NPD6705 Phase 1
0.6282 Remote Similarity NPD7525 Registered
0.6267 Remote Similarity NPD6942 Approved
0.6267 Remote Similarity NPD3702 Approved
0.6267 Remote Similarity NPD7339 Approved
0.6111 Remote Similarity NPD5360 Phase 3
0.6111 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6081 Remote Similarity NPD4243 Approved
0.6026 Remote Similarity NPD3671 Phase 1
0.5921 Remote Similarity NPD6926 Approved
0.5921 Remote Similarity NPD4785 Approved
0.5921 Remote Similarity NPD6924 Approved
0.5921 Remote Similarity NPD4784 Approved
0.5904 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5867 Remote Similarity NPD5777 Approved
0.5867 Remote Similarity NPD4758 Discontinued
0.5854 Remote Similarity NPD4788 Approved
0.5844 Remote Similarity NPD5275 Approved
0.5844 Remote Similarity NPD4190 Phase 3
0.5833 Remote Similarity NPD4224 Phase 2
0.5833 Remote Similarity NPD388 Approved
0.5833 Remote Similarity NPD386 Approved
0.5811 Remote Similarity NPD6922 Approved
0.5811 Remote Similarity NPD6923 Approved
0.5795 Remote Similarity NPD4202 Approved
0.5795 Remote Similarity NPD8171 Discontinued
0.5783 Remote Similarity NPD3665 Phase 1
0.5783 Remote Similarity NPD3666 Approved
0.5783 Remote Similarity NPD3133 Approved
0.5775 Remote Similarity NPD371 Approved
0.5769 Remote Similarity NPD6933 Approved
0.5765 Remote Similarity NPD4751 Clinical (unspecified phase)
0.5738 Remote Similarity NPD343 Approved
0.5738 Remote Similarity NPD344 Approved
0.5738 Remote Similarity NPD345 Approved
0.5733 Remote Similarity NPD7144 Approved
0.5733 Remote Similarity NPD7143 Approved
0.5658 Remote Similarity NPD7151 Approved
0.5658 Remote Similarity NPD7150 Approved
0.5658 Remote Similarity NPD7152 Approved
0.5658 Remote Similarity NPD6081 Approved
0.5647 Remote Similarity NPD3618 Phase 1
0.5632 Remote Similarity NPD5328 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