Structure

Physi-Chem Properties

Molecular Weight:  272.25
Volume:  335.374
LogP:  6.089
LogD:  5.018
LogS:  -5.751
# Rotatable Bonds:  6
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.486
Synthetic Accessibility Score:  4.346
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.604
MDCK Permeability:  1.7575430319993757e-05
Pgp-inhibitor:  0.977
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.954
30% Bioavailability (F30%):  0.743

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.305
Plasma Protein Binding (PPB):  94.65995025634766%
Volume Distribution (VD):  2.68
Pgp-substrate:  3.315378427505493%

ADMET: Metabolism

CYP1A2-inhibitor:  0.217
CYP1A2-substrate:  0.781
CYP2C19-inhibitor:  0.287
CYP2C19-substrate:  0.922
CYP2C9-inhibitor:  0.228
CYP2C9-substrate:  0.776
CYP2D6-inhibitor:  0.354
CYP2D6-substrate:  0.934
CYP3A4-inhibitor:  0.898
CYP3A4-substrate:  0.359

ADMET: Excretion

Clearance (CL):  3.634
Half-life (T1/2):  0.177

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.115
Drug-inuced Liver Injury (DILI):  0.026
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.008
Maximum Recommended Daily Dose:  0.866
Skin Sensitization:  0.835
Carcinogencity:  0.12
Eye Corrosion:  0.981
Eye Irritation:  0.978
Respiratory Toxicity:  0.065

Download Data

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

  Natural Product: NPC124851

Natural Product ID:  NPC124851
Common Name*:   Ineleganene
IUPAC Name:   (1R,2R,4S)-1-ethenyl-1-methyl-4-[(2Z)-6-methylhepta-2,6-dien-2-yl]-2-prop-1-en-2-ylcyclohexane
Synonyms:   Ineleganene
Standard InCHIKey:  DAGCNSBIYQRVRH-XEHYYXMLSA-N
Standard InCHI:  InChI=1S/C20H32/c1-8-20(7)13-12-18(14-19(20)16(4)5)17(6)11-9-10-15(2)3/h8,11,18-19H,1-2,4,9-10,12-14H2,3,5-7H3/b17-11-/t18-,19+,20-/m0/s1
SMILES:  C=C[C@@]1(C)CC[C@@H](C[C@@H]1C(=C)C)/C(=CCCC(=C)C)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL524286
PubChem CID:   10754687
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO8310 Sinularia inelegans Species Alcyoniidae Eukaryota n.a. formosan soft coral n.a. PMID[10869216]
NPO8310 Sinularia inelegans Species Alcyoniidae 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
NPT81 Cell Line A549 Homo sapiens GI50 = 3.63 ug.mL-1 PMID[464812]
NPT168 Cell Line P388 Mus musculus GI50 = 0.2 ug.mL-1 PMID[464812]

☑ 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 NPC124851 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
0.9348 High Similarity NPC22765
0.9348 High Similarity NPC17518
0.8864 High Similarity NPC105246
0.8864 High Similarity NPC190232
0.8696 High Similarity NPC86683
0.8298 Intermediate Similarity NPC296337
0.8298 Intermediate Similarity NPC241784
0.8298 Intermediate Similarity NPC114239
0.8298 Intermediate Similarity NPC13991
0.8269 Intermediate Similarity NPC469770
0.8261 Intermediate Similarity NPC192529
0.8148 Intermediate Similarity NPC469769
0.8125 Intermediate Similarity NPC323445
0.8085 Intermediate Similarity NPC202189
0.8085 Intermediate Similarity NPC248411
0.8043 Intermediate Similarity NPC193180
0.7925 Intermediate Similarity NPC123194
0.7917 Intermediate Similarity NPC49088
0.7857 Intermediate Similarity NPC176621
0.7826 Intermediate Similarity NPC103290
0.78 Intermediate Similarity NPC17810
0.766 Intermediate Similarity NPC177470
0.7647 Intermediate Similarity NPC200129
0.7636 Intermediate Similarity NPC11130
0.7636 Intermediate Similarity NPC474457
0.7636 Intermediate Similarity NPC474415
0.7636 Intermediate Similarity NPC474528
0.7636 Intermediate Similarity NPC475696
0.7609 Intermediate Similarity NPC78551
0.7609 Intermediate Similarity NPC227632
0.7609 Intermediate Similarity NPC62086
0.7593 Intermediate Similarity NPC470893
0.7586 Intermediate Similarity NPC283247
0.7556 Intermediate Similarity NPC139717
0.7556 Intermediate Similarity NPC229262
0.7556 Intermediate Similarity NPC297643
0.7547 Intermediate Similarity NPC476679
0.75 Intermediate Similarity NPC60772
0.75 Intermediate Similarity NPC86538
0.75 Intermediate Similarity NPC92224
0.75 Intermediate Similarity NPC109813
0.75 Intermediate Similarity NPC60556
0.7447 Intermediate Similarity NPC144023
0.7414 Intermediate Similarity NPC60565
0.7414 Intermediate Similarity NPC469728
0.7368 Intermediate Similarity NPC474420
0.7368 Intermediate Similarity NPC474454
0.7368 Intermediate Similarity NPC475716
0.7368 Intermediate Similarity NPC474455
0.7358 Intermediate Similarity NPC473728
0.7333 Intermediate Similarity NPC76145
0.7333 Intermediate Similarity NPC34764
0.7333 Intermediate Similarity NPC190810
0.7288 Intermediate Similarity NPC474086
0.7234 Intermediate Similarity NPC183670
0.7222 Intermediate Similarity NPC127944
0.7213 Intermediate Similarity NPC476039
0.7213 Intermediate Similarity NPC222366
0.7213 Intermediate Similarity NPC250977
0.7213 Intermediate Similarity NPC279434
0.7213 Intermediate Similarity NPC286669
0.7174 Intermediate Similarity NPC266298
0.7167 Intermediate Similarity NPC469662
0.7119 Intermediate Similarity NPC219621
0.7097 Intermediate Similarity NPC176107
0.7097 Intermediate Similarity NPC197805
0.7091 Intermediate Similarity NPC5626
0.7083 Intermediate Similarity NPC120926
0.7083 Intermediate Similarity NPC218918
0.7049 Intermediate Similarity NPC163678
0.7 Intermediate Similarity NPC202118
0.7 Intermediate Similarity NPC197238
0.6981 Remote Similarity NPC476681
0.6964 Remote Similarity NPC200258
0.6949 Remote Similarity NPC311809
0.6939 Remote Similarity NPC473912
0.6935 Remote Similarity NPC149680
0.6935 Remote Similarity NPC242945
0.6935 Remote Similarity NPC92327
0.6935 Remote Similarity NPC259156
0.6935 Remote Similarity NPC176171
0.6923 Remote Similarity NPC178644
0.6909 Remote Similarity NPC14002
0.6909 Remote Similarity NPC474416
0.6885 Remote Similarity NPC329698
0.6875 Remote Similarity NPC476431
0.6875 Remote Similarity NPC182815
0.6842 Remote Similarity NPC39068
0.6809 Remote Similarity NPC45727
0.6809 Remote Similarity NPC239039
0.6809 Remote Similarity NPC48638
0.68 Remote Similarity NPC227670
0.68 Remote Similarity NPC141777
0.68 Remote Similarity NPC166362
0.678 Remote Similarity NPC309825
0.678 Remote Similarity NPC472827
0.6774 Remote Similarity NPC107258
0.6774 Remote Similarity NPC268039
0.6769 Remote Similarity NPC475728
0.6739 Remote Similarity NPC282119
0.6724 Remote Similarity NPC470370
0.6724 Remote Similarity NPC115385
0.6724 Remote Similarity NPC470369
0.6719 Remote Similarity NPC82477
0.6719 Remote Similarity NPC142754
0.6719 Remote Similarity NPC94192
0.6719 Remote Similarity NPC296697
0.6719 Remote Similarity NPC208999
0.6719 Remote Similarity NPC260474
0.6719 Remote Similarity NPC39157
0.6719 Remote Similarity NPC188292
0.6719 Remote Similarity NPC20610
0.6719 Remote Similarity NPC476945
0.6719 Remote Similarity NPC216460
0.6719 Remote Similarity NPC160209
0.6719 Remote Similarity NPC32055
0.6667 Remote Similarity NPC317778
0.6667 Remote Similarity NPC185587
0.6667 Remote Similarity NPC470078
0.6667 Remote Similarity NPC37792
0.6667 Remote Similarity NPC323005
0.6667 Remote Similarity NPC127582
0.6667 Remote Similarity NPC115023
0.6615 Remote Similarity NPC256846
0.6615 Remote Similarity NPC286814
0.6613 Remote Similarity NPC52449
0.6613 Remote Similarity NPC285371
0.6613 Remote Similarity NPC225415
0.6613 Remote Similarity NPC475124
0.6613 Remote Similarity NPC169275
0.6613 Remote Similarity NPC290367
0.6613 Remote Similarity NPC473959
0.6607 Remote Similarity NPC23117
0.6591 Remote Similarity NPC66577
0.6591 Remote Similarity NPC206088
0.6591 Remote Similarity NPC151719
0.6591 Remote Similarity NPC471327
0.6567 Remote Similarity NPC251705
0.6567 Remote Similarity NPC471799
0.6567 Remote Similarity NPC470044
0.6567 Remote Similarity NPC470045
0.6567 Remote Similarity NPC182717
0.6562 Remote Similarity NPC114651
0.6562 Remote Similarity NPC69649
0.6562 Remote Similarity NPC68703
0.6562 Remote Similarity NPC20181
0.6562 Remote Similarity NPC193770
0.6562 Remote Similarity NPC220210
0.6557 Remote Similarity NPC41160
0.6552 Remote Similarity NPC249645
0.6552 Remote Similarity NPC55412
0.6538 Remote Similarity NPC229403
0.6531 Remote Similarity NPC246165
0.6515 Remote Similarity NPC35734
0.6515 Remote Similarity NPC34834
0.6515 Remote Similarity NPC282593
0.6515 Remote Similarity NPC159577
0.6515 Remote Similarity NPC40574
0.6515 Remote Similarity NPC214770
0.6515 Remote Similarity NPC145498
0.6515 Remote Similarity NPC477856
0.6508 Remote Similarity NPC64123
0.6508 Remote Similarity NPC251118
0.65 Remote Similarity NPC276764
0.65 Remote Similarity NPC472304
0.6491 Remote Similarity NPC476683
0.6471 Remote Similarity NPC471797
0.6471 Remote Similarity NPC329866
0.6471 Remote Similarity NPC474796
0.6471 Remote Similarity NPC474797
0.6471 Remote Similarity NPC104644
0.6462 Remote Similarity NPC310992
0.6462 Remote Similarity NPC87141
0.6452 Remote Similarity NPC174956
0.6452 Remote Similarity NPC145715
0.6444 Remote Similarity NPC213749
0.6441 Remote Similarity NPC230823
0.6441 Remote Similarity NPC281986
0.6441 Remote Similarity NPC321568
0.6441 Remote Similarity NPC22019
0.6441 Remote Similarity NPC208749
0.6429 Remote Similarity NPC306195
0.6429 Remote Similarity NPC35519
0.6429 Remote Similarity NPC179169
0.6429 Remote Similarity NPC181255
0.6429 Remote Similarity NPC157781
0.6418 Remote Similarity NPC160817
0.6418 Remote Similarity NPC242001
0.6418 Remote Similarity NPC167706
0.6418 Remote Similarity NPC234707
0.6418 Remote Similarity NPC54123
0.6418 Remote Similarity NPC265789
0.6418 Remote Similarity NPC110799
0.6418 Remote Similarity NPC190035
0.6418 Remote Similarity NPC21773
0.6418 Remote Similarity NPC225467
0.6393 Remote Similarity NPC135648
0.6393 Remote Similarity NPC323153
0.6377 Remote Similarity NPC293803
0.6377 Remote Similarity NPC473171

  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 NPC124851 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
0.8864 High Similarity NPD1799 Clinical (unspecified phase)
0.78 Intermediate Similarity NPD8262 Approved
0.7333 Intermediate Similarity NPD319 Phase 1
0.6552 Remote Similarity NPD4219 Approved
0.6515 Remote Similarity NPD6938 Clinical (unspecified phase)
0.6515 Remote Similarity NPD6939 Phase 2
0.6471 Remote Similarity NPD4784 Approved
0.6471 Remote Similarity NPD4785 Approved
0.6462 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6418 Remote Similarity NPD4243 Approved
0.6364 Remote Similarity NPD4137 Phase 3
0.6333 Remote Similarity NPD287 Approved
0.6269 Remote Similarity NPD4747 Approved
0.6269 Remote Similarity NPD4691 Approved
0.6269 Remote Similarity NPD7144 Approved
0.6269 Remote Similarity NPD7143 Approved
0.6232 Remote Similarity NPD4058 Approved
0.6232 Remote Similarity NPD5733 Approved
0.6232 Remote Similarity NPD4687 Approved
0.6176 Remote Similarity NPD7151 Approved
0.6176 Remote Similarity NPD7152 Approved
0.6176 Remote Similarity NPD7150 Approved
0.6143 Remote Similarity NPD7339 Approved
0.6143 Remote Similarity NPD6942 Approved
0.6119 Remote Similarity NPD6922 Approved
0.6119 Remote Similarity NPD6923 Approved
0.6094 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6032 Remote Similarity NPD4192 Approved
0.6032 Remote Similarity NPD4193 Approved
0.6032 Remote Similarity NPD4194 Approved
0.6032 Remote Similarity NPD4191 Approved
0.5942 Remote Similarity NPD5276 Approved
0.5915 Remote Similarity NPD4190 Phase 3
0.5915 Remote Similarity NPD8264 Approved
0.5915 Remote Similarity NPD5275 Approved
0.5833 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5811 Remote Similarity NPD4195 Approved
0.5811 Remote Similarity NPD7645 Phase 2
0.5775 Remote Similarity NPD6926 Approved
0.5775 Remote Similarity NPD6924 Approved
0.5753 Remote Similarity NPD6932 Approved
0.5733 Remote Similarity NPD7525 Registered
0.5676 Remote Similarity NPD7145 Approved
0.5676 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5616 Remote Similarity NPD6933 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