Structure

Physi-Chem Properties

Molecular Weight:  166.14
Volume:  193.773
LogP:  2.881
LogD:  2.907
LogS:  -2.908
# Rotatable Bonds:  2
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.455
Synthetic Accessibility Score:  3.082
Fsp3:  0.727
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.535
MDCK Permeability:  2.05222222575685e-05
Pgp-inhibitor:  0.254
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.853
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.986
Plasma Protein Binding (PPB):  63.12113952636719%
Volume Distribution (VD):  3.799
Pgp-substrate:  24.971712112426758%

ADMET: Metabolism

CYP1A2-inhibitor:  0.178
CYP1A2-substrate:  0.674
CYP2C19-inhibitor:  0.124
CYP2C19-substrate:  0.739
CYP2C9-inhibitor:  0.062
CYP2C9-substrate:  0.851
CYP2D6-inhibitor:  0.085
CYP2D6-substrate:  0.61
CYP3A4-inhibitor:  0.033
CYP3A4-substrate:  0.24

ADMET: Excretion

Clearance (CL):  8.316
Half-life (T1/2):  0.36

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.051
Drug-inuced Liver Injury (DILI):  0.041
AMES Toxicity:  0.803
Rat Oral Acute Toxicity:  0.056
Maximum Recommended Daily Dose:  0.03
Skin Sensitization:  0.948
Carcinogencity:  0.632
Eye Corrosion:  0.989
Eye Irritation:  0.986
Respiratory Toxicity:  0.78

Download Data

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

  Natural Product: NPC22182

Natural Product ID:  NPC22182
Common Name*:   2-(2,6,6-Trimethylcyclohexen-1-Yl)Acetaldehyde
IUPAC Name:   2-(2,6,6-trimethylcyclohexen-1-yl)acetaldehyde
Synonyms:  
Standard InCHIKey:  VHTFHZGAMYUZEP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H18O/c1-9-5-4-7-11(2,3)10(9)6-8-12/h8H,4-7H2,1-3H3
SMILES:  CC1=C(CC=O)C(C)(C)CCC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3184950
PubChem CID:   61124
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000124] Aldehydes
            • [CHEMONTID:0002434] Alpha-hydrogen aldehydes

*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
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. aerial part n.a. PMID[21070010]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[21070010]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8650.1 Perilla frutescens var. arguta Varieties 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
NPT2 Others Unspecified Potency n.a. 346.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21872.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19331.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24336.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 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 NPC22182 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
0.96 High Similarity NPC250539
0.88 High Similarity NPC116906
0.7742 Intermediate Similarity NPC193770
0.7742 Intermediate Similarity NPC4370
0.7742 Intermediate Similarity NPC290350
0.7705 Intermediate Similarity NPC268039
0.7619 Intermediate Similarity NPC155198
0.7586 Intermediate Similarity NPC56905
0.7586 Intermediate Similarity NPC27610
0.75 Intermediate Similarity NPC276009
0.75 Intermediate Similarity NPC209431
0.75 Intermediate Similarity NPC100809
0.75 Intermediate Similarity NPC195246
0.75 Intermediate Similarity NPC22098
0.7414 Intermediate Similarity NPC192427
0.7414 Intermediate Similarity NPC321568
0.7414 Intermediate Similarity NPC208749
0.7414 Intermediate Similarity NPC281986
0.7414 Intermediate Similarity NPC22019
0.7333 Intermediate Similarity NPC127582
0.7273 Intermediate Similarity NPC304983
0.7273 Intermediate Similarity NPC236623
0.7273 Intermediate Similarity NPC474562
0.7213 Intermediate Similarity NPC213152
0.7193 Intermediate Similarity NPC95581
0.7164 Intermediate Similarity NPC261316
0.7164 Intermediate Similarity NPC49737
0.7119 Intermediate Similarity NPC115385
0.7097 Intermediate Similarity NPC202118
0.7097 Intermediate Similarity NPC288253
0.7097 Intermediate Similarity NPC197238
0.7069 Intermediate Similarity NPC188789
0.7059 Intermediate Similarity NPC128346
0.7059 Intermediate Similarity NPC211641
0.7059 Intermediate Similarity NPC219232
0.6984 Remote Similarity NPC469662
0.6984 Remote Similarity NPC475124
0.6984 Remote Similarity NPC169275
0.6984 Remote Similarity NPC52449
0.6984 Remote Similarity NPC285371
0.6984 Remote Similarity NPC212210
0.6984 Remote Similarity NPC6697
0.6981 Remote Similarity NPC239754
0.6964 Remote Similarity NPC64866
0.6964 Remote Similarity NPC30433
0.6964 Remote Similarity NPC234829
0.6935 Remote Similarity NPC60565
0.6923 Remote Similarity NPC106819
0.6885 Remote Similarity NPC472304
0.6885 Remote Similarity NPC276764
0.6866 Remote Similarity NPC173321
0.6857 Remote Similarity NPC19907
0.6852 Remote Similarity NPC14917
0.6852 Remote Similarity NPC4079
0.6852 Remote Similarity NPC110234
0.6852 Remote Similarity NPC44363
0.6852 Remote Similarity NPC163751
0.6852 Remote Similarity NPC236355
0.6833 Remote Similarity NPC230823
0.6833 Remote Similarity NPC55004
0.6833 Remote Similarity NPC267626
0.6833 Remote Similarity NPC49575
0.6825 Remote Similarity NPC472306
0.6825 Remote Similarity NPC165695
0.6825 Remote Similarity NPC32285
0.6792 Remote Similarity NPC114841
0.6786 Remote Similarity NPC32351
0.6786 Remote Similarity NPC228776
0.678 Remote Similarity NPC200258
0.6735 Remote Similarity NPC69245
0.6727 Remote Similarity NPC91962
0.6724 Remote Similarity NPC474141
0.6724 Remote Similarity NPC69898
0.6724 Remote Similarity NPC295777
0.6724 Remote Similarity NPC268564
0.6721 Remote Similarity NPC266295
0.6721 Remote Similarity NPC94991
0.6721 Remote Similarity NPC308108
0.6721 Remote Similarity NPC30215
0.6721 Remote Similarity NPC311852
0.6721 Remote Similarity NPC170799
0.6719 Remote Similarity NPC4638
0.6716 Remote Similarity NPC61702
0.6716 Remote Similarity NPC162867
0.6667 Remote Similarity NPC27438
0.6667 Remote Similarity NPC20181
0.6667 Remote Similarity NPC475523
0.6667 Remote Similarity NPC115515
0.6667 Remote Similarity NPC220210
0.662 Remote Similarity NPC469796
0.662 Remote Similarity NPC469793
0.6615 Remote Similarity NPC251118
0.6613 Remote Similarity NPC285594
0.6613 Remote Similarity NPC259261
0.6613 Remote Similarity NPC96551
0.661 Remote Similarity NPC202850
0.661 Remote Similarity NPC63396
0.6575 Remote Similarity NPC170793
0.6575 Remote Similarity NPC90965
0.6575 Remote Similarity NPC152061
0.6571 Remote Similarity NPC470299
0.6567 Remote Similarity NPC87141
0.6567 Remote Similarity NPC20610
0.6567 Remote Similarity NPC260474
0.6567 Remote Similarity NPC82477
0.6567 Remote Similarity NPC188292
0.6567 Remote Similarity NPC45264
0.6567 Remote Similarity NPC296697
0.6567 Remote Similarity NPC142754
0.6567 Remote Similarity NPC310992
0.6567 Remote Similarity NPC39157
0.6515 Remote Similarity NPC323005
0.6508 Remote Similarity NPC25853
0.65 Remote Similarity NPC275472
0.6486 Remote Similarity NPC474509
0.6486 Remote Similarity NPC474956
0.6479 Remote Similarity NPC228978
0.6479 Remote Similarity NPC114236
0.6471 Remote Similarity NPC182815
0.6471 Remote Similarity NPC286814
0.6471 Remote Similarity NPC256846
0.6471 Remote Similarity NPC139397
0.6441 Remote Similarity NPC23117
0.6441 Remote Similarity NPC37644
0.6441 Remote Similarity NPC296311
0.6438 Remote Similarity NPC59436
0.6438 Remote Similarity NPC228911
0.6418 Remote Similarity NPC96962
0.6418 Remote Similarity NPC472875
0.6406 Remote Similarity NPC475795
0.6406 Remote Similarity NPC97322
0.6393 Remote Similarity NPC20603
0.6393 Remote Similarity NPC55412
0.6393 Remote Similarity NPC249645
0.6393 Remote Similarity NPC473733
0.6389 Remote Similarity NPC470525
0.6389 Remote Similarity NPC152754
0.6389 Remote Similarity NPC476987
0.6389 Remote Similarity NPC59602
0.6389 Remote Similarity NPC27205
0.6389 Remote Similarity NPC263582
0.6377 Remote Similarity NPC159577
0.6377 Remote Similarity NPC251929
0.6377 Remote Similarity NPC35734
0.6377 Remote Similarity NPC282593
0.6377 Remote Similarity NPC246722
0.6377 Remote Similarity NPC265782
0.6377 Remote Similarity NPC151045
0.6377 Remote Similarity NPC2634
0.6377 Remote Similarity NPC260040
0.6377 Remote Similarity NPC307176
0.6364 Remote Similarity NPC183422
0.6364 Remote Similarity NPC470329
0.6346 Remote Similarity NPC48930
0.6338 Remote Similarity NPC166797
0.6338 Remote Similarity NPC306928
0.6327 Remote Similarity NPC218357
0.6316 Remote Similarity NPC470813
0.6308 Remote Similarity NPC167256
0.6301 Remote Similarity NPC316500
0.6301 Remote Similarity NPC325946
0.6301 Remote Similarity NPC197659
0.6301 Remote Similarity NPC74995
0.6296 Remote Similarity NPC192529
0.629 Remote Similarity NPC193695
0.6286 Remote Similarity NPC5701
0.6286 Remote Similarity NPC115023
0.6286 Remote Similarity NPC223187
0.6286 Remote Similarity NPC84790
0.6286 Remote Similarity NPC190035
0.6286 Remote Similarity NPC72343
0.6286 Remote Similarity NPC160817
0.6286 Remote Similarity NPC470078
0.6286 Remote Similarity NPC257618
0.6286 Remote Similarity NPC181204
0.6286 Remote Similarity NPC54123
0.625 Remote Similarity NPC270042
0.625 Remote Similarity NPC65650
0.6234 Remote Similarity NPC8091
0.6234 Remote Similarity NPC307258
0.6234 Remote Similarity NPC474748
0.6232 Remote Similarity NPC261398
0.6232 Remote Similarity NPC469677
0.6216 Remote Similarity NPC35574
0.6216 Remote Similarity NPC80088
0.6216 Remote Similarity NPC4827
0.6216 Remote Similarity NPC82635
0.6216 Remote Similarity NPC62336
0.6216 Remote Similarity NPC471220
0.6216 Remote Similarity NPC178852
0.6216 Remote Similarity NPC253561
0.6216 Remote Similarity NPC475994
0.6212 Remote Similarity NPC226066
0.6212 Remote Similarity NPC473902
0.6212 Remote Similarity NPC150162
0.6207 Remote Similarity NPC176819
0.6207 Remote Similarity NPC58970
0.6207 Remote Similarity NPC163984
0.6197 Remote Similarity NPC474488
0.6197 Remote Similarity NPC109576

  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 NPC22182 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
0.6721 Remote Similarity NPD287 Approved
0.6567 Remote Similarity NPD3621 Clinical (unspecified phase)
0.65 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6479 Remote Similarity NPD8039 Approved
0.6471 Remote Similarity NPD4137 Phase 3
0.6393 Remote Similarity NPD4219 Approved
0.6377 Remote Similarity NPD4747 Approved
0.6377 Remote Similarity NPD4691 Approved
0.6286 Remote Similarity NPD5276 Approved
0.6212 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6119 Remote Similarity NPD7341 Phase 2
0.6111 Remote Similarity NPD5733 Approved
0.6111 Remote Similarity NPD4058 Approved
0.6111 Remote Similarity NPD4687 Approved
0.6029 Remote Similarity NPD7331 Phase 2
0.5909 Remote Similarity NPD4194 Approved
0.5909 Remote Similarity NPD4191 Approved
0.5909 Remote Similarity NPD4193 Approved
0.5909 Remote Similarity NPD4192 Approved
0.5897 Remote Similarity NPD3667 Approved
0.5844 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5789 Remote Similarity NPD3617 Approved
0.5763 Remote Similarity NPD8262 Approved
0.575 Remote Similarity NPD3133 Approved
0.575 Remote Similarity NPD4786 Approved
0.575 Remote Similarity NPD3666 Approved
0.575 Remote Similarity NPD3665 Phase 1
0.575 Remote Similarity NPD3668 Phase 3
0.5696 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5641 Remote Similarity NPD4695 Discontinued
0.561 Remote Similarity NPD5330 Approved
0.561 Remote Similarity NPD7334 Approved
0.561 Remote Similarity NPD5279 Phase 3
0.561 Remote Similarity NPD6684 Approved
0.561 Remote Similarity NPD3618 Phase 1
0.561 Remote Similarity NPD7521 Approved
0.561 Remote Similarity NPD6409 Approved
0.561 Remote Similarity NPD7146 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