Structure

Physi-Chem Properties

Molecular Weight:  154.14
Volume:  179.114
LogP:  3.153
LogD:  3.112
LogS:  -3.079
# Rotatable Bonds:  2
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.605
Synthetic Accessibility Score:  3.849
Fsp3:  0.8
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:  -4.305
MDCK Permeability:  1.445175803382881e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.058
30% Bioavailability (F30%):  0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.982
Plasma Protein Binding (PPB):  81.29736328125%
Volume Distribution (VD):  2.195
Pgp-substrate:  23.011653900146484%

ADMET: Metabolism

CYP1A2-inhibitor:  0.264
CYP1A2-substrate:  0.266
CYP2C19-inhibitor:  0.062
CYP2C19-substrate:  0.857
CYP2C9-inhibitor:  0.045
CYP2C9-substrate:  0.422
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.319
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.288

ADMET: Excretion

Clearance (CL):  12.388
Half-life (T1/2):  0.234

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.5
Drug-inuced Liver Injury (DILI):  0.072
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.064
Maximum Recommended Daily Dose:  0.028
Skin Sensitization:  0.081
Carcinogencity:  0.037
Eye Corrosion:  0.018
Eye Irritation:  0.435
Respiratory Toxicity:  0.212

Download Data

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

  Natural Product: NPC62755

Natural Product ID:  NPC62755
Common Name*:   Chrysanthemyl Alcohol
IUPAC Name:   [2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methanol
Synonyms:  
Standard InCHIKey:  HIPIENNKVJCMAP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H18O/c1-7(2)5-8-9(6-11)10(8,3)4/h5,8-9,11H,6H2,1-4H3
SMILES:  CC(=CC1C(CO)C1(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1318346
PubChem CID:   110685
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001563] Monocyclic 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
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ 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
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 1778.3 nM PMID[449401]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 19952.6 nM PMID[449401]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 106.81 % PMID[449402]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 105.24 % PMID[449402]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[449403]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[449403]

☑ 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 NPC62755 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
0.8511 High Similarity NPC210560
0.8511 High Similarity NPC24824
0.8511 High Similarity NPC165651
0.7778 Intermediate Similarity NPC67367
0.75 Intermediate Similarity NPC61503
0.7391 Intermediate Similarity NPC34873
0.7391 Intermediate Similarity NPC40434
0.7368 Intermediate Similarity NPC10017
0.7347 Intermediate Similarity NPC269862
0.7321 Intermediate Similarity NPC252860
0.7321 Intermediate Similarity NPC48891
0.7292 Intermediate Similarity NPC188596
0.7222 Intermediate Similarity NPC35756
0.717 Intermediate Similarity NPC329773
0.7167 Intermediate Similarity NPC211291
0.7167 Intermediate Similarity NPC133368
0.7167 Intermediate Similarity NPC473759
0.7167 Intermediate Similarity NPC474155
0.7143 Intermediate Similarity NPC298299
0.7143 Intermediate Similarity NPC148216
0.7143 Intermediate Similarity NPC251666
0.7143 Intermediate Similarity NPC148163
0.7143 Intermediate Similarity NPC130209
0.7143 Intermediate Similarity NPC232247
0.7069 Intermediate Similarity NPC155025
0.7059 Intermediate Similarity NPC87439
0.7059 Intermediate Similarity NPC140501
0.7049 Intermediate Similarity NPC107540
0.7049 Intermediate Similarity NPC475704
0.7049 Intermediate Similarity NPC309300
0.7049 Intermediate Similarity NPC225415
0.7049 Intermediate Similarity NPC290367
0.7037 Intermediate Similarity NPC244038
0.7037 Intermediate Similarity NPC26906
0.7037 Intermediate Similarity NPC214584
0.7 Intermediate Similarity NPC149682
0.6964 Remote Similarity NPC286752
0.6949 Remote Similarity NPC475931
0.6935 Remote Similarity NPC238352
0.6935 Remote Similarity NPC477009
0.6935 Remote Similarity NPC19569
0.6909 Remote Similarity NPC71506
0.6909 Remote Similarity NPC177112
0.6909 Remote Similarity NPC181255
0.6909 Remote Similarity NPC306195
0.6909 Remote Similarity NPC157781
0.6909 Remote Similarity NPC179169
0.6909 Remote Similarity NPC35519
0.6897 Remote Similarity NPC11130
0.6875 Remote Similarity NPC255042
0.6875 Remote Similarity NPC103213
0.6875 Remote Similarity NPC182840
0.6875 Remote Similarity NPC29091
0.6852 Remote Similarity NPC182102
0.6852 Remote Similarity NPC26960
0.6852 Remote Similarity NPC474460
0.6833 Remote Similarity NPC47840
0.6833 Remote Similarity NPC234264
0.6833 Remote Similarity NPC66020
0.6833 Remote Similarity NPC471081
0.6833 Remote Similarity NPC99487
0.6825 Remote Similarity NPC135650
0.6825 Remote Similarity NPC222366
0.6825 Remote Similarity NPC149680
0.6825 Remote Similarity NPC162309
0.6825 Remote Similarity NPC476039
0.6825 Remote Similarity NPC286669
0.6818 Remote Similarity NPC471662
0.68 Remote Similarity NPC194586
0.68 Remote Similarity NPC51758
0.68 Remote Similarity NPC67761
0.68 Remote Similarity NPC209279
0.68 Remote Similarity NPC108494
0.68 Remote Similarity NPC88079
0.68 Remote Similarity NPC180871
0.68 Remote Similarity NPC68889
0.6786 Remote Similarity NPC165755
0.678 Remote Similarity NPC181872
0.678 Remote Similarity NPC226848
0.6721 Remote Similarity NPC225342
0.6721 Remote Similarity NPC207007
0.6721 Remote Similarity NPC68679
0.6721 Remote Similarity NPC321867
0.6721 Remote Similarity NPC475251
0.6721 Remote Similarity NPC274704
0.6719 Remote Similarity NPC68703
0.6719 Remote Similarity NPC477791
0.6719 Remote Similarity NPC136813
0.6719 Remote Similarity NPC69649
0.6719 Remote Similarity NPC114651
0.6719 Remote Similarity NPC197805
0.6719 Remote Similarity NPC171225
0.6667 Remote Similarity NPC163678
0.6667 Remote Similarity NPC252978
0.6667 Remote Similarity NPC234597
0.6667 Remote Similarity NPC116934
0.6667 Remote Similarity NPC122239
0.6667 Remote Similarity NPC187619
0.6667 Remote Similarity NPC286154
0.6667 Remote Similarity NPC5698
0.6667 Remote Similarity NPC309825
0.6667 Remote Similarity NPC86538
0.6618 Remote Similarity NPC471659
0.6615 Remote Similarity NPC208999
0.6615 Remote Similarity NPC160209
0.6615 Remote Similarity NPC96484
0.6615 Remote Similarity NPC117804
0.6615 Remote Similarity NPC216460
0.6615 Remote Similarity NPC167527
0.6613 Remote Similarity NPC279200
0.6613 Remote Similarity NPC473508
0.6613 Remote Similarity NPC124112
0.6607 Remote Similarity NPC68014
0.66 Remote Similarity NPC269823
0.6567 Remote Similarity NPC474884
0.6562 Remote Similarity NPC250977
0.6557 Remote Similarity NPC323153
0.6557 Remote Similarity NPC135648
0.6557 Remote Similarity NPC252809
0.6557 Remote Similarity NPC240506
0.6552 Remote Similarity NPC329686
0.6552 Remote Similarity NPC281590
0.6552 Remote Similarity NPC227135
0.6545 Remote Similarity NPC289388
0.6538 Remote Similarity NPC248411
0.6522 Remote Similarity NPC474885
0.6515 Remote Similarity NPC473893
0.6515 Remote Similarity NPC471560
0.6515 Remote Similarity NPC474248
0.6515 Remote Similarity NPC269877
0.6515 Remote Similarity NPC167272
0.6508 Remote Similarity NPC110241
0.6508 Remote Similarity NPC300593
0.6508 Remote Similarity NPC96793
0.6508 Remote Similarity NPC323424
0.65 Remote Similarity NPC475830
0.6471 Remote Similarity NPC213538
0.6471 Remote Similarity NPC329763
0.6471 Remote Similarity NPC256766
0.6452 Remote Similarity NPC210346
0.6441 Remote Similarity NPC249645
0.6441 Remote Similarity NPC55412
0.6429 Remote Similarity NPC473672
0.6429 Remote Similarity NPC244452
0.6429 Remote Similarity NPC471658
0.6429 Remote Similarity NPC474495
0.6418 Remote Similarity NPC145498
0.6418 Remote Similarity NPC92801
0.6418 Remote Similarity NPC34834
0.6418 Remote Similarity NPC9161
0.6418 Remote Similarity NPC49422
0.6415 Remote Similarity NPC76976
0.6415 Remote Similarity NPC296337
0.6415 Remote Similarity NPC160628
0.6406 Remote Similarity NPC471200
0.6379 Remote Similarity NPC95581
0.6364 Remote Similarity NPC32055
0.6364 Remote Similarity NPC471238
0.6349 Remote Similarity NPC474480
0.6346 Remote Similarity NPC106819
0.6338 Remote Similarity NPC476007
0.6338 Remote Similarity NPC34019
0.6333 Remote Similarity NPC278550
0.6333 Remote Similarity NPC52012
0.6333 Remote Similarity NPC71755
0.6324 Remote Similarity NPC242001
0.6324 Remote Similarity NPC164022
0.6324 Remote Similarity NPC41886
0.6324 Remote Similarity NPC95863
0.6324 Remote Similarity NPC469343
0.6324 Remote Similarity NPC167706
0.6324 Remote Similarity NPC477792
0.6316 Remote Similarity NPC170167
0.6308 Remote Similarity NPC272125
0.6308 Remote Similarity NPC326310
0.6308 Remote Similarity NPC202017
0.6308 Remote Similarity NPC267027
0.6308 Remote Similarity NPC311736
0.6296 Remote Similarity NPC22098
0.6296 Remote Similarity NPC276009
0.6296 Remote Similarity NPC195246
0.6271 Remote Similarity NPC218525
0.6271 Remote Similarity NPC223604
0.6269 Remote Similarity NPC90115
0.6269 Remote Similarity NPC217570
0.625 Remote Similarity NPC61665
0.625 Remote Similarity NPC312328
0.625 Remote Similarity NPC302041
0.625 Remote Similarity NPC65897
0.625 Remote Similarity NPC288381
0.625 Remote Similarity NPC85346
0.625 Remote Similarity NPC140233
0.625 Remote Similarity NPC225974
0.625 Remote Similarity NPC287744
0.625 Remote Similarity NPC20934
0.6232 Remote Similarity NPC471799
0.6232 Remote Similarity NPC68443
0.6232 Remote Similarity NPC474140
0.6232 Remote Similarity NPC14352
0.6232 Remote Similarity NPC182717

  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 NPC62755 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
0.7143 Intermediate Similarity NPD342 Phase 1
0.7059 Intermediate Similarity NPD4265 Approved
0.6721 Remote Similarity NPD368 Approved
0.6515 Remote Similarity NPD6923 Approved
0.6515 Remote Similarity NPD6922 Approved
0.6441 Remote Similarity NPD4219 Approved
0.6418 Remote Similarity NPD7144 Approved
0.6418 Remote Similarity NPD7143 Approved
0.6324 Remote Similarity NPD7152 Approved
0.6324 Remote Similarity NPD7150 Approved
0.6324 Remote Similarity NPD7151 Approved
0.6143 Remote Similarity NPD6926 Approved
0.6143 Remote Similarity NPD6924 Approved
0.6056 Remote Similarity NPD8264 Approved
0.6056 Remote Similarity NPD6942 Approved
0.6056 Remote Similarity NPD7339 Approved
0.6 Remote Similarity NPD6902 Approved
0.5972 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5972 Remote Similarity NPD6933 Approved
0.589 Remote Similarity NPD6925 Approved
0.589 Remote Similarity NPD5776 Phase 2
0.589 Remote Similarity NPD6932 Approved
0.5811 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5811 Remote Similarity NPD7145 Approved
0.58 Remote Similarity NPD319 Phase 1
0.5775 Remote Similarity NPD4732 Discontinued
0.5733 Remote Similarity NPD6929 Approved
0.5733 Remote Similarity NPD7645 Phase 2
0.5733 Remote Similarity NPD6683 Phase 2
0.5658 Remote Similarity NPD6930 Phase 2
0.5658 Remote Similarity NPD7514 Phase 3
0.5658 Remote Similarity NPD7332 Phase 2
0.5658 Remote Similarity NPD7525 Registered
0.5658 Remote Similarity NPD7509 Discontinued
0.5658 Remote Similarity NPD6931 Approved
0.5634 Remote Similarity NPD4243 Approved
0.5625 Remote Similarity NPD571 Approved
0.56 Remote Similarity NPD5784 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