Structure

Physi-Chem Properties

Molecular Weight:  206.2
Volume:  248.247
LogP:  5.609
LogD:  4.266
LogS:  -4.863
# Rotatable Bonds:  0
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.492
Synthetic Accessibility Score:  3.642
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.569
MDCK Permeability:  1.4012030078447424e-05
Pgp-inhibitor:  0.669
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.984
30% Bioavailability (F30%):  0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.165
Plasma Protein Binding (PPB):  97.09891510009766%
Volume Distribution (VD):  3.765
Pgp-substrate:  2.783643960952759%

ADMET: Metabolism

CYP1A2-inhibitor:  0.291
CYP1A2-substrate:  0.647
CYP2C19-inhibitor:  0.341
CYP2C19-substrate:  0.945
CYP2C9-inhibitor:  0.276
CYP2C9-substrate:  0.545
CYP2D6-inhibitor:  0.026
CYP2D6-substrate:  0.266
CYP3A4-inhibitor:  0.285
CYP3A4-substrate:  0.324

ADMET: Excretion

Clearance (CL):  15.957
Half-life (T1/2):  0.06

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.078
Drug-inuced Liver Injury (DILI):  0.116
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.108
Maximum Recommended Daily Dose:  0.103
Skin Sensitization:  0.609
Carcinogencity:  0.163
Eye Corrosion:  0.984
Eye Irritation:  0.932
Respiratory Toxicity:  0.77

Download Data

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

  Natural Product: NPC192529

Natural Product ID:  NPC192529
Common Name*:   (+)-Drim-8-Ene
IUPAC Name:   (4aS,8aS)-4,4,7,8,8a-pentamethyl-1,2,3,4a,5,6-hexahydronaphthalene
Synonyms:  
Standard InCHIKey:  VSURQKXDWDMWKL-DZGCQCFKSA-N
Standard InCHI:  InChI=1S/C15H26/c1-11-7-8-13-14(3,4)9-6-10-15(13,5)12(11)2/h13H,6-10H2,1-5H3/t13-,15+/m0/s1
SMILES:  CC1=C(C)[C@@]2([C@@H](CC1)C(C)(C)CCC2)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1097316
PubChem CID:   46888523
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002837] Hydrocarbons
      • [CHEMONTID:0004475] Unsaturated hydrocarbons
        • [CHEMONTID:0004622] Branched unsaturated hydrocarbons

*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
NPO30398 Acacia pennata Species Fabaceae Eukaryota n.a. leaf n.a. PMID[17823873]
NPO30398 Acacia pennata Species Fabaceae Eukaryota leaves n.a. n.a. PMID[20450170]

☑ 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
NPT461 Cell Line PANC-1 Homo sapiens IC50 = 15100.0 nM PMID[554312]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 23200.0 nM PMID[554312]
NPT2 Others Unspecified IC50 = 13500.0 nM PMID[554312]
NPT27 Others Unspecified IC50 > 100000.0 nM PMID[554312]

☑ 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 NPC192529 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
0.907 High Similarity NPC86683
0.8889 High Similarity NPC17518
0.8478 Intermediate Similarity NPC22765
0.8409 Intermediate Similarity NPC202189
0.8372 Intermediate Similarity NPC193180
0.8261 Intermediate Similarity NPC124851
0.8222 Intermediate Similarity NPC13991
0.8222 Intermediate Similarity NPC296337
0.8222 Intermediate Similarity NPC114239
0.8222 Intermediate Similarity NPC241784
0.814 Intermediate Similarity NPC103290
0.8 Intermediate Similarity NPC248411
0.7955 Intermediate Similarity NPC190232
0.7955 Intermediate Similarity NPC105246
0.7917 Intermediate Similarity NPC200129
0.7843 Intermediate Similarity NPC123194
0.7843 Intermediate Similarity NPC469770
0.76 Intermediate Similarity NPC473728
0.7547 Intermediate Similarity NPC474415
0.7547 Intermediate Similarity NPC474528
0.7547 Intermediate Similarity NPC475696
0.75 Intermediate Similarity NPC78551
0.75 Intermediate Similarity NPC227632
0.75 Intermediate Similarity NPC62086
0.7442 Intermediate Similarity NPC297643
0.7442 Intermediate Similarity NPC229262
0.7442 Intermediate Similarity NPC139717
0.7407 Intermediate Similarity NPC469769
0.7358 Intermediate Similarity NPC179024
0.7273 Intermediate Similarity NPC474454
0.7273 Intermediate Similarity NPC475716
0.7273 Intermediate Similarity NPC474420
0.7273 Intermediate Similarity NPC474455
0.7222 Intermediate Similarity NPC474457
0.7209 Intermediate Similarity NPC76145
0.7209 Intermediate Similarity NPC34764
0.7209 Intermediate Similarity NPC190810
0.7174 Intermediate Similarity NPC177470
0.7021 Intermediate Similarity NPC60556
0.7021 Intermediate Similarity NPC109813
0.7021 Intermediate Similarity NPC86538
0.7018 Intermediate Similarity NPC469728
0.7 Intermediate Similarity NPC17810
0.6957 Remote Similarity NPC144023
0.6909 Remote Similarity NPC470369
0.6909 Remote Similarity NPC470370
0.6863 Remote Similarity NPC476681
0.6852 Remote Similarity NPC470893
0.6842 Remote Similarity NPC127582
0.6842 Remote Similarity NPC311809
0.6792 Remote Similarity NPC474416
0.6792 Remote Similarity NPC127944
0.6786 Remote Similarity NPC56905
0.6786 Remote Similarity NPC60772
0.6786 Remote Similarity NPC27610
0.678 Remote Similarity NPC475124
0.678 Remote Similarity NPC285371
0.678 Remote Similarity NPC469662
0.6739 Remote Similarity NPC183670
0.6735 Remote Similarity NPC49088
0.6667 Remote Similarity NPC163678
0.6667 Remote Similarity NPC227670
0.6667 Remote Similarity NPC166362
0.6667 Remote Similarity NPC141777
0.6667 Remote Similarity NPC239039
0.6667 Remote Similarity NPC5626
0.6667 Remote Similarity NPC472827
0.6667 Remote Similarity NPC472304
0.6667 Remote Similarity NPC276764
0.661 Remote Similarity NPC197238
0.661 Remote Similarity NPC202118
0.661 Remote Similarity NPC474086
0.6607 Remote Similarity NPC11130
0.66 Remote Similarity NPC323445
0.6557 Remote Similarity NPC242945
0.6557 Remote Similarity NPC176171
0.6557 Remote Similarity NPC286669
0.6557 Remote Similarity NPC476039
0.6557 Remote Similarity NPC92327
0.6557 Remote Similarity NPC259156
0.6557 Remote Similarity NPC222366
0.6557 Remote Similarity NPC279434
0.6552 Remote Similarity NPC176621
0.6538 Remote Similarity NPC116906
0.6481 Remote Similarity NPC14002
0.6481 Remote Similarity NPC23117
0.6481 Remote Similarity NPC476679
0.6458 Remote Similarity NPC473912
0.6452 Remote Similarity NPC20181
0.6452 Remote Similarity NPC193770
0.6452 Remote Similarity NPC290350
0.6452 Remote Similarity NPC220210
0.6452 Remote Similarity NPC176107
0.6452 Remote Similarity NPC171225
0.6452 Remote Similarity NPC4370
0.6452 Remote Similarity NPC197805
0.6441 Remote Similarity NPC282694
0.6441 Remote Similarity NPC219621
0.6441 Remote Similarity NPC79576
0.6441 Remote Similarity NPC194208
0.6441 Remote Similarity NPC60565
0.6429 Remote Similarity NPC264779
0.64 Remote Similarity NPC229403
0.6383 Remote Similarity NPC246165
0.6379 Remote Similarity NPC309825
0.6364 Remote Similarity NPC476683
0.6349 Remote Similarity NPC142754
0.6349 Remote Similarity NPC310992
0.6349 Remote Similarity NPC82477
0.6349 Remote Similarity NPC208999
0.6349 Remote Similarity NPC260474
0.6349 Remote Similarity NPC39157
0.6349 Remote Similarity NPC476945
0.6349 Remote Similarity NPC188292
0.6349 Remote Similarity NPC20610
0.6349 Remote Similarity NPC32055
0.6349 Remote Similarity NPC296697
0.6349 Remote Similarity NPC216460
0.6333 Remote Similarity NPC145715
0.6333 Remote Similarity NPC81615
0.6333 Remote Similarity NPC174956
0.6333 Remote Similarity NPC472306
0.6333 Remote Similarity NPC283247
0.6316 Remote Similarity NPC115385
0.6316 Remote Similarity NPC192427
0.6304 Remote Similarity NPC48638
0.6304 Remote Similarity NPC45727
0.6296 Remote Similarity NPC22182
0.6296 Remote Similarity NPC179169
0.6296 Remote Similarity NPC181255
0.6296 Remote Similarity NPC157781
0.6296 Remote Similarity NPC35519
0.6296 Remote Similarity NPC306195
0.629 Remote Similarity NPC323005
0.6279 Remote Similarity NPC213749
0.6271 Remote Similarity NPC135648
0.6271 Remote Similarity NPC317778
0.625 Remote Similarity NPC286814
0.625 Remote Similarity NPC138409
0.625 Remote Similarity NPC139397
0.625 Remote Similarity NPC218918
0.625 Remote Similarity NPC474248
0.625 Remote Similarity NPC182815
0.625 Remote Similarity NPC200258
0.625 Remote Similarity NPC184919
0.625 Remote Similarity NPC120926
0.623 Remote Similarity NPC169275
0.623 Remote Similarity NPC323424
0.623 Remote Similarity NPC6697
0.623 Remote Similarity NPC52449
0.623 Remote Similarity NPC96793
0.623 Remote Similarity NPC473959
0.6222 Remote Similarity NPC92224
0.6207 Remote Similarity NPC474769
0.6207 Remote Similarity NPC189290
0.6207 Remote Similarity NPC308108
0.6207 Remote Similarity NPC170799
0.6182 Remote Similarity NPC69898
0.6182 Remote Similarity NPC295777
0.6167 Remote Similarity NPC213152
0.6154 Remote Similarity NPC475728
0.6154 Remote Similarity NPC178644
0.6154 Remote Similarity NPC282593
0.6154 Remote Similarity NPC260040
0.6154 Remote Similarity NPC92801
0.6154 Remote Similarity NPC251929
0.6154 Remote Similarity NPC35734
0.6154 Remote Similarity NPC2634
0.6154 Remote Similarity NPC307176
0.6154 Remote Similarity NPC34834
0.6154 Remote Similarity NPC265782
0.6154 Remote Similarity NPC159577
0.614 Remote Similarity NPC39068
0.6129 Remote Similarity NPC251118
0.6129 Remote Similarity NPC268039
0.6129 Remote Similarity NPC107258
0.6111 Remote Similarity NPC214584
0.6111 Remote Similarity NPC26906
0.6111 Remote Similarity NPC471681
0.6111 Remote Similarity NPC236623
0.6102 Remote Similarity NPC152211
0.6102 Remote Similarity NPC28755
0.6094 Remote Similarity NPC155198
0.6094 Remote Similarity NPC160209
0.6094 Remote Similarity NPC94192
0.6094 Remote Similarity NPC87141
0.6094 Remote Similarity NPC96484
0.6071 Remote Similarity NPC250539
0.6066 Remote Similarity NPC288253
0.6061 Remote Similarity NPC470078
0.6061 Remote Similarity NPC110799
0.6061 Remote Similarity NPC223187
0.6061 Remote Similarity NPC474562
0.6061 Remote Similarity NPC21773
0.6061 Remote Similarity NPC164022
0.6061 Remote Similarity NPC265789
0.6061 Remote Similarity NPC54123
0.6061 Remote Similarity NPC190035
0.6061 Remote Similarity NPC115023
0.6061 Remote Similarity NPC160817

  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 NPC192529 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
0.7955 Intermediate Similarity NPD1799 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD319 Phase 1
0.7 Intermediate Similarity NPD8262 Approved
0.6349 Remote Similarity NPD3621 Clinical (unspecified phase)
0.625 Remote Similarity NPD4137 Phase 3
0.6207 Remote Similarity NPD287 Approved
0.6154 Remote Similarity NPD6938 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4747 Approved
0.6154 Remote Similarity NPD6939 Phase 2
0.6154 Remote Similarity NPD4691 Approved
0.6061 Remote Similarity NPD4243 Approved
0.5882 Remote Similarity NPD5733 Approved
0.5882 Remote Similarity NPD4785 Approved
0.5882 Remote Similarity NPD4058 Approved
0.5882 Remote Similarity NPD4784 Approved
0.5882 Remote Similarity NPD4687 Approved
0.5862 Remote Similarity NPD4219 Approved
0.5821 Remote Similarity NPD5276 Approved
0.5797 Remote Similarity NPD7339 Approved
0.5797 Remote Similarity NPD5275 Approved
0.5797 Remote Similarity NPD4190 Phase 3
0.5797 Remote Similarity NPD6942 Approved
0.5714 Remote Similarity NPD3701 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