Structure

Physi-Chem Properties

Molecular Weight:  198.16
Volume:  222.496
LogP:  3.543
LogD:  3.83
LogS:  -3.023
# Rotatable Bonds:  3
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.637
Synthetic Accessibility Score:  3.141
Fsp3:  0.917
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.417
MDCK Permeability:  2.5863586415653117e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.922
30% Bioavailability (F30%):  0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.424
Plasma Protein Binding (PPB):  92.91848754882812%
Volume Distribution (VD):  1.247
Pgp-substrate:  6.3246026039123535%

ADMET: Metabolism

CYP1A2-inhibitor:  0.31
CYP1A2-substrate:  0.103
CYP2C19-inhibitor:  0.06
CYP2C19-substrate:  0.857
CYP2C9-inhibitor:  0.325
CYP2C9-substrate:  0.267
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.097
CYP3A4-inhibitor:  0.203
CYP3A4-substrate:  0.358

ADMET: Excretion

Clearance (CL):  4.514
Half-life (T1/2):  0.508

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.213
Drug-inuced Liver Injury (DILI):  0.89
AMES Toxicity:  0.027
Rat Oral Acute Toxicity:  0.016
Maximum Recommended Daily Dose:  0.017
Skin Sensitization:  0.883
Carcinogencity:  0.279
Eye Corrosion:  0.943
Eye Irritation:  0.974
Respiratory Toxicity:  0.262

Download Data

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

  Natural Product: NPC291724

Natural Product ID:  NPC291724
Common Name*:   (1R,2S,5R)-2-Isopropyl-5-Methylcyclohexyl Acetate
IUPAC Name:   [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] acetate
Synonyms:  
Standard InCHIKey:  XHXUANMFYXWVNG-ADEWGFFLSA-N
Standard InCHI:  InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12-/m1/s1
SMILES:  CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2236867
PubChem CID:   220674
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001401] Menthane monoterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(00)97029-8]
NPO6473.1 Perilla frutescens var. acuta Strain Lamiaceae Eukaryota n.a. n.a. n.a. PMID[10757731]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota leaves Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota Leaves and branches Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. leaf n.a. PMID[18409045]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota seeds n.a. n.a. PMID[18603435]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO29141 Panax ginseng Species Araliaceae Eukaryota flower buds n.a. n.a. PMID[19926279]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota Seeds n.a. n.a. PMID[20469887]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota leaves n.a. n.a. PMID[20584613]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. root n.a. PMID[2092947]
NPO29141 Panax ginseng Species Araliaceae Eukaryota berry n.a. n.a. PMID[21216145]
NPO28430 Biota orientalis n.a. n.a. n.a. n.a. leaf n.a. PMID[21793559]
NPO28430 Biota orientalis n.a. n.a. n.a. n.a. twig n.a. PMID[21793559]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO29141 Panax ginseng Species Araliaceae Eukaryota leaves n.a. n.a. PMID[24290061]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[24968750]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[25152999]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota roots n.a. n.a. PMID[26259802]
NPO29141 Panax ginseng Species Araliaceae Eukaryota stems-leaves n.a. n.a. PMID[26420067]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[26521454]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. stem n.a. PMID[27914541]
NPO29141 Panax ginseng Species Araliaceae Eukaryota Flower Buds n.a. n.a. PMID[28345906]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32129622]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO30242 Sterculia lychnophora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19592 Michelia alba Species Magnoliaceae 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]
NPO31056 Mentha haplocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31384 Thuja orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19054 Semen trichosanthis n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO1279 Fritillaria cirrhosa Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6473.1 Perilla frutescens var. acuta Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28430 Biota orientalis n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO30828 Mentha piperita Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23197 Juniperus oxycedrus Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15277 Pericarpium trichosanthis n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23197 Juniperus oxycedrus Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6473.1 Perilla frutescens var. acuta Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1279 Fritillaria cirrhosa Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28430 Biota orientalis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO26346 Semen sterculiae lychnophorae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19054 Semen trichosanthis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO15277 Pericarpium trichosanthis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30242 Sterculia lychnophora Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae 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]
NPO28430 Biota orientalis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31056 Mentha haplocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae 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]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1279 Fritillaria cirrhosa Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae 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]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae 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]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13434 Acremonium furcatum Species Plectosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21769 Pterocarpus dalbergioides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19830 Chamonixia caespitosa Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29141 Panax ginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22349 Cucumaria frondosa Species Cucumariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23029 Tetradenia riparia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21902 Thalictrum sachalinense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20157 Boykinia tellimoides Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11329 Echinops grijsii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28430 Biota orientalis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8789 Schizonepeta tenuifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1279 Fritillaria cirrhosa Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23197 Juniperus oxycedrus Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae 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
NPT35 Others n.a. LogP = 2.91 n.a. PMID[544986]
NPT21 Organism Aspergillus niger Aspergillus niger -logMIC = 1.98 n.a. PMID[544986]
NPT20 Organism Candida albicans Candida albicans -logMIC = 1.8 n.a. PMID[544986]
NPT19 Organism Escherichia coli Escherichia coli -logMIC = 1.5 n.a. PMID[544986]
NPT79 Organism Bacillus subtilis Bacillus subtilis -logMIC = 1.8 n.a. PMID[544986]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus -logMIC = 1.5 n.a. PMID[544986]
NPT4976 Organism Monographella nivalis var. nivalis Monographella nivalis var. nivalis Activity = 51.2 % PMID[544987]

☑ 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 NPC291724 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 NPC274261
0.8364 Intermediate Similarity NPC240206
0.807 Intermediate Similarity NPC204173
0.7895 Intermediate Similarity NPC230070
0.7895 Intermediate Similarity NPC9880
0.7895 Intermediate Similarity NPC87828
0.7759 Intermediate Similarity NPC66145
0.7647 Intermediate Similarity NPC287550
0.7647 Intermediate Similarity NPC84030
0.7647 Intermediate Similarity NPC198540
0.7647 Intermediate Similarity NPC223468
0.7647 Intermediate Similarity NPC176309
0.7647 Intermediate Similarity NPC147343
0.7627 Intermediate Similarity NPC83088
0.7447 Intermediate Similarity NPC316546
0.7407 Intermediate Similarity NPC314084
0.7368 Intermediate Similarity NPC170780
0.7302 Intermediate Similarity NPC476928
0.7193 Intermediate Similarity NPC300189
0.7167 Intermediate Similarity NPC478126
0.7049 Intermediate Similarity NPC306750
0.7015 Intermediate Similarity NPC123122
0.7015 Intermediate Similarity NPC474755
0.7015 Intermediate Similarity NPC109510
0.7015 Intermediate Similarity NPC476718
0.7 Intermediate Similarity NPC185116
0.6984 Remote Similarity NPC474768
0.6912 Remote Similarity NPC71152
0.6912 Remote Similarity NPC74639
0.6912 Remote Similarity NPC272359
0.6912 Remote Similarity NPC55508
0.6909 Remote Similarity NPC305182
0.6909 Remote Similarity NPC142103
0.6885 Remote Similarity NPC84218
0.6875 Remote Similarity NPC84562
0.6818 Remote Similarity NPC178541
0.6812 Remote Similarity NPC186851
0.6812 Remote Similarity NPC478105
0.6809 Remote Similarity NPC301398
0.6809 Remote Similarity NPC196442
0.6809 Remote Similarity NPC86545
0.6809 Remote Similarity NPC223374
0.6786 Remote Similarity NPC307022
0.678 Remote Similarity NPC210316
0.6769 Remote Similarity NPC41542
0.6731 Remote Similarity NPC302939
0.6731 Remote Similarity NPC287331
0.6731 Remote Similarity NPC144891
0.6724 Remote Similarity NPC53209
0.6716 Remote Similarity NPC168596
0.6716 Remote Similarity NPC94632
0.6714 Remote Similarity NPC469581
0.6714 Remote Similarity NPC474020
0.6714 Remote Similarity NPC471046
0.6714 Remote Similarity NPC92489
0.6714 Remote Similarity NPC136424
0.6667 Remote Similarity NPC249754
0.662 Remote Similarity NPC143250
0.662 Remote Similarity NPC471151
0.662 Remote Similarity NPC307865
0.662 Remote Similarity NPC84868
0.662 Remote Similarity NPC212453
0.662 Remote Similarity NPC476719
0.6613 Remote Similarity NPC472021
0.661 Remote Similarity NPC471269
0.6596 Remote Similarity NPC286498
0.6557 Remote Similarity NPC47663
0.6545 Remote Similarity NPC13105
0.6531 Remote Similarity NPC14608
0.6531 Remote Similarity NPC128996
0.6528 Remote Similarity NPC191345
0.6528 Remote Similarity NPC243594
0.6528 Remote Similarity NPC252483
0.6528 Remote Similarity NPC471045
0.6528 Remote Similarity NPC31031
0.6528 Remote Similarity NPC43463
0.6481 Remote Similarity NPC282440
0.6481 Remote Similarity NPC308301
0.6481 Remote Similarity NPC108441
0.6481 Remote Similarity NPC77550
0.6462 Remote Similarity NPC19311
0.6462 Remote Similarity NPC157518
0.6462 Remote Similarity NPC230047
0.6458 Remote Similarity NPC155872
0.6452 Remote Similarity NPC472020
0.6452 Remote Similarity NPC226602
0.6452 Remote Similarity NPC472019
0.6441 Remote Similarity NPC319589
0.6438 Remote Similarity NPC47808
0.6438 Remote Similarity NPC476176
0.6438 Remote Similarity NPC73013
0.6438 Remote Similarity NPC220379
0.6438 Remote Similarity NPC477287
0.6438 Remote Similarity NPC305835
0.6438 Remote Similarity NPC474754
0.6429 Remote Similarity NPC474524
0.6429 Remote Similarity NPC33876
0.6429 Remote Similarity NPC472944
0.6429 Remote Similarity NPC277993
0.6429 Remote Similarity NPC475517
0.6429 Remote Similarity NPC472945
0.6429 Remote Similarity NPC224987
0.6393 Remote Similarity NPC236588
0.6393 Remote Similarity NPC135438
0.6389 Remote Similarity NPC171658
0.6377 Remote Similarity NPC478227
0.6364 Remote Similarity NPC326957
0.6351 Remote Similarity NPC474714
0.6351 Remote Similarity NPC472943
0.6351 Remote Similarity NPC304194
0.6351 Remote Similarity NPC261616
0.6351 Remote Similarity NPC269791
0.6351 Remote Similarity NPC469580
0.6351 Remote Similarity NPC125366
0.6351 Remote Similarity NPC472951
0.6351 Remote Similarity NPC471216
0.6351 Remote Similarity NPC186594
0.6351 Remote Similarity NPC134227
0.6351 Remote Similarity NPC471217
0.6351 Remote Similarity NPC475456
0.6351 Remote Similarity NPC206735
0.6338 Remote Similarity NPC212733
0.6333 Remote Similarity NPC67508
0.6333 Remote Similarity NPC84824
0.6327 Remote Similarity NPC80641
0.6324 Remote Similarity NPC295788
0.6301 Remote Similarity NPC184737
0.6296 Remote Similarity NPC47363
0.6296 Remote Similarity NPC287231
0.629 Remote Similarity NPC475515
0.629 Remote Similarity NPC87296
0.629 Remote Similarity NPC215671
0.629 Remote Similarity NPC132998
0.6286 Remote Similarity NPC248567
0.6286 Remote Similarity NPC475230
0.6271 Remote Similarity NPC102336
0.6271 Remote Similarity NPC36002
0.6267 Remote Similarity NPC71541
0.6267 Remote Similarity NPC475743
0.6267 Remote Similarity NPC290495
0.6267 Remote Similarity NPC38642
0.6267 Remote Similarity NPC223330
0.6267 Remote Similarity NPC119922
0.6267 Remote Similarity NPC470154
0.6267 Remote Similarity NPC470156
0.6267 Remote Similarity NPC209318
0.6267 Remote Similarity NPC280781
0.6267 Remote Similarity NPC475951
0.6267 Remote Similarity NPC116320
0.6267 Remote Similarity NPC73515
0.6267 Remote Similarity NPC48756
0.6267 Remote Similarity NPC195334
0.6267 Remote Similarity NPC190940
0.6267 Remote Similarity NPC58631
0.6267 Remote Similarity NPC211049
0.625 Remote Similarity NPC4209
0.625 Remote Similarity NPC185547
0.625 Remote Similarity NPC95804
0.623 Remote Similarity NPC141699
0.6226 Remote Similarity NPC325102
0.6226 Remote Similarity NPC82843
0.6216 Remote Similarity NPC201276
0.6216 Remote Similarity NPC80891
0.6212 Remote Similarity NPC215987
0.6212 Remote Similarity NPC306805
0.6212 Remote Similarity NPC295256
0.6207 Remote Similarity NPC251335
0.6197 Remote Similarity NPC167702
0.6197 Remote Similarity NPC96759
0.6197 Remote Similarity NPC280026
0.619 Remote Similarity NPC470363
0.619 Remote Similarity NPC475821
0.6184 Remote Similarity NPC477284
0.6184 Remote Similarity NPC256112
0.6184 Remote Similarity NPC13494
0.6184 Remote Similarity NPC477446
0.6184 Remote Similarity NPC216800
0.6184 Remote Similarity NPC470155
0.6184 Remote Similarity NPC154043
0.6184 Remote Similarity NPC202688
0.6184 Remote Similarity NPC208912
0.6184 Remote Similarity NPC472504
0.6184 Remote Similarity NPC226988
0.6184 Remote Similarity NPC477286
0.6184 Remote Similarity NPC286719
0.6184 Remote Similarity NPC289486
0.6184 Remote Similarity NPC2096
0.6184 Remote Similarity NPC477447
0.6184 Remote Similarity NPC61107
0.6184 Remote Similarity NPC286786
0.6184 Remote Similarity NPC60018
0.6182 Remote Similarity NPC52700
0.6182 Remote Similarity NPC105329
0.6182 Remote Similarity NPC145045
0.6182 Remote Similarity NPC63182
0.6182 Remote Similarity NPC314679
0.6176 Remote Similarity NPC119838
0.617 Remote Similarity NPC40965
0.6164 Remote Similarity NPC143133
0.6164 Remote Similarity NPC207010

  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 NPC291724 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
0.7647 Intermediate Similarity NPD385 Approved
0.7647 Intermediate Similarity NPD384 Approved
0.6731 Remote Similarity NPD367 Approved
0.6724 Remote Similarity NPD615 Clinical (unspecified phase)
0.662 Remote Similarity NPD8144 Approved
0.662 Remote Similarity NPD8143 Approved
0.6618 Remote Similarity NPD5777 Approved
0.6562 Remote Similarity NPD371 Approved
0.6481 Remote Similarity NPD386 Approved
0.6481 Remote Similarity NPD388 Approved
0.6471 Remote Similarity NPD1460 Approved
0.6296 Remote Similarity NPD2699 Approved
0.625 Remote Similarity NPD6117 Approved
0.6226 Remote Similarity NPD1462 Approved
0.6212 Remote Similarity NPD9496 Clinical (unspecified phase)
0.6197 Remote Similarity NPD6113 Clinical (unspecified phase)
0.619 Remote Similarity NPD3198 Approved
0.6182 Remote Similarity NPD634 Phase 3
0.6176 Remote Similarity NPD229 Approved
0.6164 Remote Similarity NPD6116 Phase 1
0.6111 Remote Similarity NPD3702 Approved
0.6094 Remote Similarity NPD1145 Discontinued
0.6081 Remote Similarity NPD6114 Approved
0.6081 Remote Similarity NPD6118 Approved
0.6081 Remote Similarity NPD6697 Approved
0.6081 Remote Similarity NPD6115 Approved
0.6053 Remote Similarity NPD1780 Approved
0.6053 Remote Similarity NPD1779 Approved
0.6 Remote Similarity NPD2686 Approved
0.6 Remote Similarity NPD2687 Approved
0.6 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6 Remote Similarity NPD370 Phase 3
0.6 Remote Similarity NPD2254 Approved
0.5949 Remote Similarity NPD1694 Approved
0.5926 Remote Similarity NPD387 Clinical (unspecified phase)
0.5902 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5897 Remote Similarity NPD3669 Approved
0.5897 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5882 Remote Similarity NPD9449 Clinical (unspecified phase)
0.5882 Remote Similarity NPD4224 Phase 2
0.5857 Remote Similarity NPD3726 Approved
0.5857 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5857 Remote Similarity NPD3725 Approved
0.5857 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5821 Remote Similarity NPD7909 Approved
0.58 Remote Similarity NPD9447 Approved
0.5753 Remote Similarity NPD1811 Approved
0.5753 Remote Similarity NPD1810 Approved
0.5741 Remote Similarity NPD9426 Discontinued
0.5735 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5694 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5694 Remote Similarity NPD4808 Clinical (unspecified phase)
0.569 Remote Similarity NPD6125 Clinical (unspecified phase)
0.569 Remote Similarity NPD2266 Phase 2
0.5676 Remote Similarity NPD3703 Phase 2
0.566 Remote Similarity NPD9450 Approved
0.566 Remote Similarity NPD77 Approved
0.5658 Remote Similarity NPD4802 Phase 2
0.5658 Remote Similarity NPD4238 Approved
0.5634 Remote Similarity NPD3698 Phase 2
0.5634 Remote Similarity NPD4267 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