Structure

Physi-Chem Properties

Molecular Weight:  783.37
Volume:  786.119
LogP:  3.008
LogD:  1.73
LogS:  -2.004
# Rotatable Bonds:  10
TPSA:  207.76
# H-Bond Aceptor:  12
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.144
Synthetic Accessibility Score:  5.961
Fsp3:  0.643
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.811
MDCK Permeability:  3.7210895698081004e-06
Pgp-inhibitor:  0.037
Pgp-substrate:  0.875
Human Intestinal Absorption (HIA):  0.819
20% Bioavailability (F20%):  0.964
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  96.20391082763672%
Volume Distribution (VD):  0.714
Pgp-substrate:  3.383823871612549%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.294
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.895
CYP2C9-inhibitor:  0.073
CYP2C9-substrate:  0.677
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.108
CYP3A4-inhibitor:  0.431
CYP3A4-substrate:  0.905

ADMET: Excretion

Clearance (CL):  3.11
Half-life (T1/2):  0.117

ADMET: Toxicity

hERG Blockers:  0.194
Human Hepatotoxicity (H-HT):  0.401
Drug-inuced Liver Injury (DILI):  0.073
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.177
Maximum Recommended Daily Dose:  0.976
Skin Sensitization:  0.884
Carcinogencity:  0.004
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.2

Download Data

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

  Natural Product: NPC80738

Natural Product ID:  NPC80738
Common Name*:   ICNAROAALVLDJI-AWDNKCRRSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ICNAROAALVLDJI-AWDNKCRRSA-N
Standard InCHI:  InChI=1S/C42H57NO11S/c1-20(2)26-9-11-40(7,31(46)19-43-13-14-55(51,52)53)34(26)28-16-25(17-30(45)36(47)22(28)5)42(50)18-24-15-29(44)37(48)23(6)32-33(24)38(54-42)39(49)41(8)12-10-27(21(3)4)35(32)41/h15-17,20-21,26-27,34-35,38-39,43,49-50H,9-14,18-19H2,1-8H3,(H,44,48)(H,45,47)(H,51,52,53)/t26-,27-,34-,35-,38-,39+,40+,41-,42+/m1/s1
SMILES:  CC(C)[C@H]1CC[C@@](C)(C(=O)CNCCS(=O)(=O)O)[C@H]1c1cc(cc(c(=O)c1C)O)[C@@]1(Cc2cc(c(=O)c(C)c3c2[C@H]([C@@H]([C@]2(C)CC[C@H](C(C)C)[C@H]32)O)O1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2419839
PubChem CID:   73350759
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0000051] Aromatic 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
NPO32713 phorbas gukhulensis Species Hymedesmiidae Eukaryota n.a. Korean n.a. PMID[24025124]

☑ 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 LC50 = 110.0 nM PMID[485791]
NPT111 Cell Line K562 Homo sapiens LC50 = 320.0 nM PMID[485791]
NPT2890 Protein Complex Sodium/potassium-transporting ATPase Homo sapiens IC50 > 100000.0 nM PMID[485791]
NPT2 Others Unspecified IC50 > 100000.0 nM PMID[485791]

☑ 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 NPC80738 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
0.7872 Intermediate Similarity NPC262845
0.7872 Intermediate Similarity NPC68293
0.7589 Intermediate Similarity NPC290261
0.7464 Intermediate Similarity NPC82759
0.7092 Intermediate Similarity NPC136922
0.6507 Remote Similarity NPC176336
0.6471 Remote Similarity NPC317654
0.6471 Remote Similarity NPC473249
0.6471 Remote Similarity NPC96010
0.625 Remote Similarity NPC243902
0.625 Remote Similarity NPC473040
0.6218 Remote Similarity NPC478136
0.6174 Remote Similarity NPC475163
0.6164 Remote Similarity NPC475065
0.6159 Remote Similarity NPC311554
0.6159 Remote Similarity NPC473617
0.6159 Remote Similarity NPC473828
0.6159 Remote Similarity NPC257457
0.6139 Remote Similarity NPC478139
0.6138 Remote Similarity NPC475176
0.6129 Remote Similarity NPC3381
0.6129 Remote Similarity NPC145238
0.6118 Remote Similarity NPC473270
0.6118 Remote Similarity NPC473274
0.6101 Remote Similarity NPC189393
0.6101 Remote Similarity NPC90814
0.6096 Remote Similarity NPC318363
0.6096 Remote Similarity NPC473482
0.6096 Remote Similarity NPC475418
0.6093 Remote Similarity NPC27413
0.6093 Remote Similarity NPC59751
0.6093 Remote Similarity NPC471854
0.6093 Remote Similarity NPC271621
0.6084 Remote Similarity NPC32577
0.6084 Remote Similarity NPC114540
0.6084 Remote Similarity NPC155332
0.6081 Remote Similarity NPC475480
0.6081 Remote Similarity NPC473921
0.6081 Remote Similarity NPC475668
0.6076 Remote Similarity NPC471407
0.6074 Remote Similarity NPC250312
0.6071 Remote Similarity NPC201899
0.6071 Remote Similarity NPC471674
0.6069 Remote Similarity NPC475414
0.6069 Remote Similarity NPC173172
0.6069 Remote Similarity NPC266570
0.6067 Remote Similarity NPC147912
0.6067 Remote Similarity NPC67259
0.6062 Remote Similarity NPC476111
0.6056 Remote Similarity NPC266955
0.6053 Remote Similarity NPC470276
0.6039 Remote Similarity NPC52839
0.6039 Remote Similarity NPC473256
0.6039 Remote Similarity NPC470878
0.6037 Remote Similarity NPC471672
0.6028 Remote Similarity NPC471815
0.6027 Remote Similarity NPC330011
0.6027 Remote Similarity NPC329048
0.6027 Remote Similarity NPC473284
0.6026 Remote Similarity NPC478216
0.6014 Remote Similarity NPC475563
0.6014 Remote Similarity NPC477997
0.6014 Remote Similarity NPC475134
0.6014 Remote Similarity NPC115899
0.6013 Remote Similarity NPC19028
0.6013 Remote Similarity NPC270109
0.6013 Remote Similarity NPC35037
0.6013 Remote Similarity NPC476529
0.6013 Remote Similarity NPC9674
0.6013 Remote Similarity NPC475775
0.6 Remote Similarity NPC257017
0.6 Remote Similarity NPC473485
0.6 Remote Similarity NPC474508
0.6 Remote Similarity NPC25887
0.6 Remote Similarity NPC471855
0.6 Remote Similarity NPC5485
0.6 Remote Similarity NPC162009
0.5987 Remote Similarity NPC20302
0.5987 Remote Similarity NPC15095
0.5987 Remote Similarity NPC167606
0.5987 Remote Similarity NPC140055
0.5987 Remote Similarity NPC286528
0.5987 Remote Similarity NPC222307
0.5986 Remote Similarity NPC57079
0.5986 Remote Similarity NPC220155
0.5986 Remote Similarity NPC108368
0.5976 Remote Similarity NPC476558
0.5975 Remote Similarity NPC476966
0.5974 Remote Similarity NPC145182
0.5974 Remote Similarity NPC109607
0.5974 Remote Similarity NPC107338
0.5974 Remote Similarity NPC185876
0.5974 Remote Similarity NPC471126
0.5974 Remote Similarity NPC472076
0.5974 Remote Similarity NPC19336
0.5974 Remote Similarity NPC470312
0.5974 Remote Similarity NPC329080
0.5974 Remote Similarity NPC472075
0.5974 Remote Similarity NPC157252
0.5974 Remote Similarity NPC472759
0.5974 Remote Similarity NPC475885
0.5974 Remote Similarity NPC471128
0.5973 Remote Similarity NPC474315
0.596 Remote Similarity NPC178289
0.5959 Remote Similarity NPC189863
0.5951 Remote Similarity NPC297058
0.5948 Remote Similarity NPC315974
0.5948 Remote Similarity NPC50774
0.5948 Remote Similarity NPC709
0.5946 Remote Similarity NPC170221
0.5946 Remote Similarity NPC137911
0.5946 Remote Similarity NPC10064
0.5946 Remote Similarity NPC228477
0.5938 Remote Similarity NPC475314
0.5938 Remote Similarity NPC475606
0.5938 Remote Similarity NPC220757
0.5938 Remote Similarity NPC251564
0.5938 Remote Similarity NPC477189
0.5938 Remote Similarity NPC196921
0.5935 Remote Similarity NPC315915
0.5935 Remote Similarity NPC202051
0.5933 Remote Similarity NPC470063
0.5933 Remote Similarity NPC124358
0.5931 Remote Similarity NPC476237
0.5926 Remote Similarity NPC223356
0.5926 Remote Similarity NPC182266
0.5926 Remote Similarity NPC475154
0.5926 Remote Similarity NPC475500
0.5926 Remote Similarity NPC471136
0.5926 Remote Similarity NPC473548
0.5926 Remote Similarity NPC100017
0.5926 Remote Similarity NPC120420
0.5926 Remote Similarity NPC471137
0.5924 Remote Similarity NPC470922
0.5921 Remote Similarity NPC315652
0.5921 Remote Similarity NPC7905
0.5918 Remote Similarity NPC475294
0.5918 Remote Similarity NPC255387
0.5918 Remote Similarity NPC131665
0.5915 Remote Similarity NPC474938
0.5915 Remote Similarity NPC474785
0.5915 Remote Similarity NPC202705
0.5915 Remote Similarity NPC253826
0.5912 Remote Similarity NPC245094
0.5909 Remote Similarity NPC471108
0.5909 Remote Similarity NPC475041
0.5909 Remote Similarity NPC264954
0.5909 Remote Similarity NPC156745
0.5909 Remote Similarity NPC275696
0.5909 Remote Similarity NPC22628
0.5909 Remote Similarity NPC236918
0.5909 Remote Similarity NPC5991
0.5909 Remote Similarity NPC5989
0.5909 Remote Similarity NPC255081
0.5909 Remote Similarity NPC180640
0.5906 Remote Similarity NPC6206
0.5906 Remote Similarity NPC37116
0.5906 Remote Similarity NPC72688
0.5906 Remote Similarity NPC473627
0.5906 Remote Similarity NPC16270
0.5906 Remote Similarity NPC181298
0.5906 Remote Similarity NPC238850
0.5903 Remote Similarity NPC303559
0.5903 Remote Similarity NPC194028
0.5903 Remote Similarity NPC197447
0.5903 Remote Similarity NPC169365
0.5903 Remote Similarity NPC168319
0.5901 Remote Similarity NPC231240
0.5901 Remote Similarity NPC472769
0.5897 Remote Similarity NPC470265
0.5897 Remote Similarity NPC269642
0.5897 Remote Similarity NPC478138
0.5897 Remote Similarity NPC23786
0.5894 Remote Similarity NPC472926
0.5893 Remote Similarity NPC160222
0.5893 Remote Similarity NPC193753
0.589 Remote Similarity NPC99864
0.5886 Remote Similarity NPC120994
0.5886 Remote Similarity NPC203702
0.5882 Remote Similarity NPC473656
0.5882 Remote Similarity NPC284068
0.5882 Remote Similarity NPC312824
0.5882 Remote Similarity NPC473968
0.5882 Remote Similarity NPC476190
0.5882 Remote Similarity NPC470493
0.5882 Remote Similarity NPC183580
0.5882 Remote Similarity NPC10721
0.5882 Remote Similarity NPC470492
0.5878 Remote Similarity NPC88701
0.5875 Remote Similarity NPC162495
0.5875 Remote Similarity NPC104382
0.5875 Remote Similarity NPC35109
0.5875 Remote Similarity NPC473593
0.5875 Remote Similarity NPC472770
0.5871 Remote Similarity NPC477143
0.5871 Remote Similarity NPC473808
0.5871 Remote Similarity NPC477140
0.5871 Remote Similarity NPC474370
0.5868 Remote Similarity NPC470426
0.5867 Remote Similarity NPC100329

  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 NPC80738 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
0.6533 Remote Similarity NPD7624 Clinical (unspecified phase)
0.6533 Remote Similarity NPD7623 Phase 3
0.6471 Remote Similarity NPD7747 Phase 1
0.6471 Remote Similarity NPD7746 Phase 1
0.6467 Remote Similarity NPD7739 Clinical (unspecified phase)
0.6291 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6164 Remote Similarity NPD6845 Suspended
0.6101 Remote Similarity NPD7260 Phase 2
0.5987 Remote Similarity NPD7115 Discovery
0.5973 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5951 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5935 Remote Similarity NPD6908 Approved
0.5935 Remote Similarity NPD6909 Approved
0.589 Remote Similarity NPD8415 Approved
0.5762 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5724 Remote Similarity NPD8297 Approved
0.5671 Remote Similarity NPD8449 Approved
0.566 Remote Similarity NPD7830 Approved
0.566 Remote Similarity NPD7829 Approved
0.5655 Remote Similarity NPD4225 Approved
0.5644 Remote Similarity NPD7751 Phase 1
0.5638 Remote Similarity NPD7333 Discontinued
0.5636 Remote Similarity NPD8450 Suspended
0.5621 Remote Similarity NPD6882 Approved
0.5608 Remote Similarity NPD4754 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