Structure

Physi-Chem Properties

Molecular Weight:  218.17
Volume:  251.764
LogP:  3.446
LogD:  2.555
LogS:  -3.436
# Rotatable Bonds:  2
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.7
Synthetic Accessibility Score:  4.166
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.48
MDCK Permeability:  1.2269912076590117e-05
Pgp-inhibitor:  0.982
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.992
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.499
Plasma Protein Binding (PPB):  95.467041015625%
Volume Distribution (VD):  3.68
Pgp-substrate:  3.0335705280303955%

ADMET: Metabolism

CYP1A2-inhibitor:  0.463
CYP1A2-substrate:  0.211
CYP2C19-inhibitor:  0.237
CYP2C19-substrate:  0.806
CYP2C9-inhibitor:  0.259
CYP2C9-substrate:  0.685
CYP2D6-inhibitor:  0.034
CYP2D6-substrate:  0.13
CYP3A4-inhibitor:  0.432
CYP3A4-substrate:  0.281

ADMET: Excretion

Clearance (CL):  8.835
Half-life (T1/2):  0.729

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.121
Drug-inuced Liver Injury (DILI):  0.115
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.009
Maximum Recommended Daily Dose:  0.074
Skin Sensitization:  0.146
Carcinogencity:  0.912
Eye Corrosion:  0.223
Eye Irritation:  0.941
Respiratory Toxicity:  0.272

Download Data

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

  Natural Product: NPC298299

Natural Product ID:  NPC298299
Common Name*:   8,11-Dihydro-12-Hydroxy Isolaurene
IUPAC Name:   [4-[(1R)-1,2,3-trimethylcyclopent-2-en-1-yl]cyclohexa-1,4-dien-1-yl]methanol
Synonyms:  
Standard InCHIKey:  GMYASKWNAWMMGB-HNNXBMFYSA-N
Standard InCHI:  InChI=1S/C15H22O/c1-11-8-9-15(3,12(11)2)14-6-4-13(10-16)5-7-14/h4,7,16H,5-6,8-10H2,1-3H3/t15-/m0/s1
SMILES:  OCC1=CCC(=CC1)[C@@]1(C)CCC(=C1C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2064473
PubChem CID:   70682365
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
NPO8821 Delphinium dictyocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8821 Delphinium dictyocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2491 Laurencia obtusa Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO666 Cymbidium aloifolium Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5527 Ligularia atroviolacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10341 Pseudogymnoascus pannorum Species Pseudeurotiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2491 Laurencia obtusa Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8821 Delphinium dictyocarpum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1054 Peucedanum graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18938 Ladeania juncea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15600 Trifolium pannonicum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13493 Mauremys reevesii Species Geoemydidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2329 Scutellaria glabra Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1221 Juniperus serawschanica Species Cupressaceae 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
NPT20 Organism Candida albicans Candida albicans MIC = 120.0 ug.mL-1 PMID[555732]
NPT610 Others Molecular identity unknown MIC = 200.0 ug.mL-1 PMID[555732]
NPT185 Organism Aspergillus flavus Aspergillus flavus MIC = 1250.0 ug.mL-1 PMID[555732]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 39.0 ug.mL-1 PMID[555732]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 31.0 ug.mL-1 PMID[555732]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 79.9 % PMID[555732]

☑ 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 NPC298299 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
0.8491 Intermediate Similarity NPC244038
0.8448 Intermediate Similarity NPC471081
0.8393 Intermediate Similarity NPC48891
0.807 Intermediate Similarity NPC249645
0.807 Intermediate Similarity NPC55412
0.8033 Intermediate Similarity NPC110241
0.7966 Intermediate Similarity NPC309825
0.7903 Intermediate Similarity NPC19569
0.7895 Intermediate Similarity NPC130209
0.7895 Intermediate Similarity NPC148216
0.7895 Intermediate Similarity NPC251666
0.7895 Intermediate Similarity NPC232247
0.7895 Intermediate Similarity NPC148163
0.7833 Intermediate Similarity NPC234264
0.7833 Intermediate Similarity NPC47840
0.7778 Intermediate Similarity NPC162309
0.7679 Intermediate Similarity NPC35756
0.7656 Intermediate Similarity NPC477791
0.7636 Intermediate Similarity NPC26960
0.7636 Intermediate Similarity NPC182102
0.7627 Intermediate Similarity NPC11130
0.7619 Intermediate Similarity NPC187619
0.7581 Intermediate Similarity NPC124112
0.746 Intermediate Similarity NPC475704
0.746 Intermediate Similarity NPC107540
0.746 Intermediate Similarity NPC323424
0.746 Intermediate Similarity NPC96793
0.7419 Intermediate Similarity NPC210346
0.7385 Intermediate Similarity NPC136813
0.7385 Intermediate Similarity NPC114651
0.7385 Intermediate Similarity NPC171225
0.7353 Intermediate Similarity NPC474743
0.7302 Intermediate Similarity NPC211291
0.7302 Intermediate Similarity NPC474155
0.7302 Intermediate Similarity NPC473759
0.7302 Intermediate Similarity NPC133368
0.7273 Intermediate Similarity NPC96484
0.7273 Intermediate Similarity NPC167527
0.7258 Intermediate Similarity NPC66020
0.7258 Intermediate Similarity NPC240506
0.7231 Intermediate Similarity NPC135650
0.7222 Intermediate Similarity NPC24824
0.7222 Intermediate Similarity NPC210560
0.7222 Intermediate Similarity NPC165651
0.7213 Intermediate Similarity NPC10017
0.7193 Intermediate Similarity NPC474495
0.7193 Intermediate Similarity NPC473672
0.7188 Intermediate Similarity NPC309300
0.7164 Intermediate Similarity NPC90115
0.7164 Intermediate Similarity NPC473893
0.7164 Intermediate Similarity NPC471560
0.7164 Intermediate Similarity NPC474248
0.7164 Intermediate Similarity NPC217570
0.7143 Intermediate Similarity NPC62755
0.7143 Intermediate Similarity NPC475251
0.7143 Intermediate Similarity NPC321867
0.7143 Intermediate Similarity NPC68679
0.7143 Intermediate Similarity NPC207007
0.7121 Intermediate Similarity NPC68703
0.7121 Intermediate Similarity NPC69649
0.7097 Intermediate Similarity NPC122239
0.7059 Intermediate Similarity NPC34834
0.7059 Intermediate Similarity NPC255042
0.7059 Intermediate Similarity NPC103213
0.7059 Intermediate Similarity NPC29091
0.7059 Intermediate Similarity NPC182840
0.7042 Intermediate Similarity NPC244488
0.7042 Intermediate Similarity NPC247325
0.7031 Intermediate Similarity NPC81615
0.7031 Intermediate Similarity NPC83200
0.7018 Intermediate Similarity NPC474460
0.7015 Intermediate Similarity NPC117804
0.7 Intermediate Similarity NPC329686
0.697 Remote Similarity NPC326310
0.697 Remote Similarity NPC202017
0.697 Remote Similarity NPC267027
0.6957 Remote Similarity NPC471662
0.6935 Remote Similarity NPC181872
0.6935 Remote Similarity NPC475830
0.6935 Remote Similarity NPC226848
0.6935 Remote Similarity NPC155025
0.6923 Remote Similarity NPC290367
0.6909 Remote Similarity NPC140501
0.6901 Remote Similarity NPC23231
0.6901 Remote Similarity NPC60818
0.6875 Remote Similarity NPC274704
0.6875 Remote Similarity NPC260573
0.6866 Remote Similarity NPC269985
0.6866 Remote Similarity NPC82337
0.6866 Remote Similarity NPC106613
0.6857 Remote Similarity NPC234527
0.6857 Remote Similarity NPC14352
0.6852 Remote Similarity NPC116934
0.6852 Remote Similarity NPC269862
0.6825 Remote Similarity NPC475931
0.6818 Remote Similarity NPC287339
0.6818 Remote Similarity NPC477009
0.6818 Remote Similarity NPC238352
0.6812 Remote Similarity NPC189745
0.6792 Remote Similarity NPC269823
0.6792 Remote Similarity NPC188596
0.678 Remote Similarity NPC306195
0.678 Remote Similarity NPC179169
0.678 Remote Similarity NPC157781
0.678 Remote Similarity NPC68014
0.678 Remote Similarity NPC35519
0.678 Remote Similarity NPC181255
0.6769 Remote Similarity NPC474480
0.6769 Remote Similarity NPC279200
0.6769 Remote Similarity NPC473508
0.6765 Remote Similarity NPC471238
0.6765 Remote Similarity NPC224532
0.6765 Remote Similarity NPC160209
0.6761 Remote Similarity NPC309178
0.6761 Remote Similarity NPC469593
0.6761 Remote Similarity NPC469534
0.6761 Remote Similarity NPC471659
0.6761 Remote Similarity NPC469533
0.6757 Remote Similarity NPC84694
0.6757 Remote Similarity NPC28862
0.6757 Remote Similarity NPC81306
0.6757 Remote Similarity NPC31258
0.6757 Remote Similarity NPC209430
0.6757 Remote Similarity NPC47982
0.6757 Remote Similarity NPC143182
0.6757 Remote Similarity NPC109546
0.6757 Remote Similarity NPC30986
0.6731 Remote Similarity NPC15934
0.6721 Remote Similarity NPC227135
0.6719 Remote Similarity NPC99487
0.6719 Remote Similarity NPC135648
0.6716 Remote Similarity NPC222366
0.6716 Remote Similarity NPC286669
0.6716 Remote Similarity NPC476039
0.6714 Remote Similarity NPC95863
0.6714 Remote Similarity NPC469343
0.6714 Remote Similarity NPC477792
0.6712 Remote Similarity NPC473756
0.6712 Remote Similarity NPC262747
0.6667 Remote Similarity NPC269877
0.6667 Remote Similarity NPC225415
0.6667 Remote Similarity NPC474496
0.6667 Remote Similarity NPC300593
0.6667 Remote Similarity NPC194586
0.6667 Remote Similarity NPC213538
0.6667 Remote Similarity NPC69383
0.6667 Remote Similarity NPC68889
0.6667 Remote Similarity NPC180871
0.6667 Remote Similarity NPC51758
0.6667 Remote Similarity NPC171148
0.6667 Remote Similarity NPC256766
0.6667 Remote Similarity NPC209279
0.6667 Remote Similarity NPC167272
0.6667 Remote Similarity NPC474011
0.6667 Remote Similarity NPC313179
0.6667 Remote Similarity NPC263698
0.6667 Remote Similarity NPC67761
0.6667 Remote Similarity NPC88079
0.6667 Remote Similarity NPC234193
0.6667 Remote Similarity NPC108494
0.6667 Remote Similarity NPC313185
0.6622 Remote Similarity NPC209135
0.6622 Remote Similarity NPC474816
0.6622 Remote Similarity NPC474216
0.662 Remote Similarity NPC29542
0.662 Remote Similarity NPC130665
0.662 Remote Similarity NPC474140
0.662 Remote Similarity NPC323437
0.662 Remote Similarity NPC186042
0.662 Remote Similarity NPC201562
0.6618 Remote Similarity NPC45782
0.6618 Remote Similarity NPC96962
0.6618 Remote Similarity NPC197805
0.6615 Remote Similarity NPC329416
0.6615 Remote Similarity NPC317177
0.6615 Remote Similarity NPC225342
0.6615 Remote Similarity NPC326645
0.6615 Remote Similarity NPC469728
0.6615 Remote Similarity NPC317025
0.6613 Remote Similarity NPC474643
0.6613 Remote Similarity NPC473865
0.661 Remote Similarity NPC214584
0.661 Remote Similarity NPC151782
0.661 Remote Similarity NPC26906
0.6607 Remote Similarity NPC87439
0.6607 Remote Similarity NPC269074
0.6607 Remote Similarity NPC160628
0.6579 Remote Similarity NPC209620
0.6579 Remote Similarity NPC23852
0.6579 Remote Similarity NPC264245
0.6575 Remote Similarity NPC471658
0.6575 Remote Similarity NPC310643
0.6575 Remote Similarity NPC253190
0.6575 Remote Similarity NPC126969
0.6571 Remote Similarity NPC9161
0.6571 Remote Similarity NPC49422
0.6571 Remote Similarity NPC254845
0.6571 Remote Similarity NPC286154
0.6567 Remote Similarity NPC163678
0.6567 Remote Similarity NPC308844

  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 NPC298299 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
0.807 Intermediate Similarity NPD4219 Approved
0.7895 Intermediate Similarity NPD342 Phase 1
0.7143 Intermediate Similarity NPD368 Approved
0.6909 Remote Similarity NPD4265 Approved
0.6849 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6922 Approved
0.6667 Remote Similarity NPD7332 Phase 2
0.6667 Remote Similarity NPD6923 Approved
0.6667 Remote Similarity NPD8264 Approved
0.6615 Remote Similarity NPD4193 Approved
0.6615 Remote Similarity NPD4192 Approved
0.6615 Remote Similarity NPD4191 Approved
0.6615 Remote Similarity NPD4194 Approved
0.6571 Remote Similarity NPD7144 Approved
0.6571 Remote Similarity NPD7143 Approved
0.6486 Remote Similarity NPD5776 Phase 2
0.6486 Remote Similarity NPD6925 Approved
0.6479 Remote Similarity NPD7150 Approved
0.6479 Remote Similarity NPD7151 Approved
0.6479 Remote Similarity NPD7152 Approved
0.6447 Remote Similarity NPD7514 Phase 3
0.6438 Remote Similarity NPD7339 Approved
0.6438 Remote Similarity NPD6942 Approved
0.64 Remote Similarity NPD7145 Approved
0.6389 Remote Similarity NPD4732 Discontinued
0.6364 Remote Similarity NPD6898 Phase 1
0.6364 Remote Similarity NPD6902 Approved
0.6351 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6929 Approved
0.6301 Remote Similarity NPD6924 Approved
0.6301 Remote Similarity NPD6926 Approved
0.6234 Remote Similarity NPD6931 Approved
0.6234 Remote Similarity NPD6930 Phase 2
0.6184 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6176 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6133 Remote Similarity NPD6933 Approved
0.6125 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6098 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6053 Remote Similarity NPD6932 Approved
0.6049 Remote Similarity NPD1696 Phase 3
0.6038 Remote Similarity NPD319 Phase 1
0.6027 Remote Similarity NPD4243 Approved
0.6026 Remote Similarity NPD7509 Discontinued
0.6 Remote Similarity NPD6695 Phase 3
0.5926 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5897 Remote Similarity NPD6683 Phase 2
0.5875 Remote Similarity NPD3667 Approved
0.5867 Remote Similarity NPD4784 Approved
0.5867 Remote Similarity NPD4785 Approved
0.5854 Remote Similarity NPD6893 Approved
0.5823 Remote Similarity NPD7525 Registered
0.5802 Remote Similarity NPD5362 Discontinued
0.5802 Remote Similarity NPD7154 Phase 3
0.5789 Remote Similarity NPD5275 Approved
0.5789 Remote Similarity NPD4190 Phase 3
0.5769 Remote Similarity NPD4271 Approved
0.5769 Remote Similarity NPD4268 Approved
0.5753 Remote Similarity NPD791 Approved
0.5753 Remote Similarity NPD15 Approved
0.5738 Remote Similarity NPD8262 Approved
0.5732 Remote Similarity NPD3665 Phase 1
0.5732 Remote Similarity NPD3666 Approved
0.5732 Remote Similarity NPD4786 Approved
0.5732 Remote Similarity NPD3133 Approved
0.5714 Remote Similarity NPD7524 Approved
0.5714 Remote Similarity NPD7750 Discontinued
0.5698 Remote Similarity NPD7136 Phase 2
0.5696 Remote Similarity NPD7645 Phase 2
0.5632 Remote Similarity NPD7637 Suspended
0.5625 Remote Similarity NPD4822 Approved
0.5625 Remote Similarity NPD4820 Approved
0.5625 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4821 Approved
0.5625 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4252 Approved
0.5625 Remote Similarity NPD4819 Approved
0.561 Remote Similarity NPD5331 Approved
0.561 Remote Similarity NPD5332 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