Structure

Physi-Chem Properties

Molecular Weight:  496.08
Volume:  402.535
LogP:  3.134
LogD:  3.158
LogS:  -4.112
# Rotatable Bonds:  1
TPSA:  80.92
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.418
Synthetic Accessibility Score:  5.442
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.08
MDCK Permeability:  1.5555911886622198e-05
Pgp-inhibitor:  0.027
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.106
20% Bioavailability (F20%):  0.139
30% Bioavailability (F30%):  0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.667
Plasma Protein Binding (PPB):  83.3545913696289%
Volume Distribution (VD):  1.003
Pgp-substrate:  24.21401596069336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.045
CYP1A2-substrate:  0.832
CYP2C19-inhibitor:  0.522
CYP2C19-substrate:  0.872
CYP2C9-inhibitor:  0.78
CYP2C9-substrate:  0.139
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.068
CYP3A4-inhibitor:  0.859
CYP3A4-substrate:  0.913

ADMET: Excretion

Clearance (CL):  4.463
Half-life (T1/2):  0.363

ADMET: Toxicity

hERG Blockers:  0.054
Human Hepatotoxicity (H-HT):  0.47
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.194
Rat Oral Acute Toxicity:  0.964
Maximum Recommended Daily Dose:  0.958
Skin Sensitization:  0.765
Carcinogencity:  0.968
Eye Corrosion:  0.884
Eye Irritation:  0.185
Respiratory Toxicity:  0.966

Download Data

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

  Natural Product: NPC475817

Natural Product ID:  NPC475817
Common Name*:   Neoirietetraol
IUPAC Name:   (1R,4S,4aS,7R,8aR)-4-bromo-7-[(1R,3R,5S)-3-bromo-5-hydroxy-1,2,2-trimethylcyclopentyl]-1,4a-dimethyl-2,3,4,5,6,8-hexahydronaphthalene-1,7,8a-triol
Synonyms:   Neoirietetraol
Standard InCHIKey:  DNRSHPZOBKEHNQ-AWJYIKAYSA-N
Standard InCHI:  InChI=1S/C20H34Br2O4/c1-15(2)13(22)10-14(23)18(15,5)19(25)9-8-16(3)12(21)6-7-17(4,24)20(16,26)11-19/h12-14,23-26H,6-11H2,1-5H3/t12-,13+,14-,16+,17+,18-,19+,20+/m0/s1
SMILES:  Br[C@@H]1C[C@@H]([C@](C1(C)C)(C)[C@@]1(O)CC[C@]2([C@@](C1)(O)[C@](C)(O)CC[C@@H]2Br)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL516664
PubChem CID:   637399
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
NPO33110 laurencia yonaguniensis Species Rhodomelaceae Eukaryota n.a. Okinawan n.a. PMID[11908989]

☑ 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
NPT176 Organism Artemia salina Artemia salina LC50 = 40100.0 nM PMID[550423]

☑ 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 NPC475817 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
0.8023 Intermediate Similarity NPC329871
0.7791 Intermediate Similarity NPC477227
0.7791 Intermediate Similarity NPC192046
0.7791 Intermediate Similarity NPC302578
0.7791 Intermediate Similarity NPC128951
0.7791 Intermediate Similarity NPC105208
0.7701 Intermediate Similarity NPC67657
0.7701 Intermediate Similarity NPC18857
0.7674 Intermediate Similarity NPC163597
0.7647 Intermediate Similarity NPC475793
0.7647 Intermediate Similarity NPC237510
0.7614 Intermediate Similarity NPC269333
0.7586 Intermediate Similarity NPC185915
0.7558 Intermediate Similarity NPC476424
0.7558 Intermediate Similarity NPC243027
0.7558 Intermediate Similarity NPC158208
0.7558 Intermediate Similarity NPC196136
0.7558 Intermediate Similarity NPC317242
0.7442 Intermediate Similarity NPC10476
0.7442 Intermediate Similarity NPC304499
0.7442 Intermediate Similarity NPC192501
0.7442 Intermediate Similarity NPC228994
0.7416 Intermediate Similarity NPC287452
0.7326 Intermediate Similarity NPC153719
0.7326 Intermediate Similarity NPC470610
0.7326 Intermediate Similarity NPC476422
0.7312 Intermediate Similarity NPC313115
0.7303 Intermediate Similarity NPC147993
0.7283 Intermediate Similarity NPC478054
0.7273 Intermediate Similarity NPC475934
0.7262 Intermediate Similarity NPC474756
0.7241 Intermediate Similarity NPC48795
0.7241 Intermediate Similarity NPC475458
0.72 Intermediate Similarity NPC92231
0.72 Intermediate Similarity NPC34732
0.7176 Intermediate Similarity NPC470833
0.7128 Intermediate Similarity NPC266651
0.71 Intermediate Similarity NPC156912
0.7093 Intermediate Similarity NPC232925
0.7093 Intermediate Similarity NPC251201
0.7093 Intermediate Similarity NPC63588
0.7053 Intermediate Similarity NPC121981
0.7033 Intermediate Similarity NPC477282
0.7033 Intermediate Similarity NPC81074
0.701 Intermediate Similarity NPC224552
0.701 Intermediate Similarity NPC239453
0.6989 Remote Similarity NPC60018
0.6989 Remote Similarity NPC475388
0.6989 Remote Similarity NPC154043
0.6989 Remote Similarity NPC202688
0.6979 Remote Similarity NPC5943
0.6977 Remote Similarity NPC107919
0.6977 Remote Similarity NPC477820
0.6977 Remote Similarity NPC66407
0.6966 Remote Similarity NPC139765
0.6966 Remote Similarity NPC131584
0.6957 Remote Similarity NPC16449
0.6915 Remote Similarity NPC216420
0.6915 Remote Similarity NPC163616
0.6915 Remote Similarity NPC211135
0.6915 Remote Similarity NPC85095
0.6905 Remote Similarity NPC472946
0.6875 Remote Similarity NPC131365
0.6854 Remote Similarity NPC470151
0.6842 Remote Similarity NPC255882
0.6842 Remote Similarity NPC320824
0.6837 Remote Similarity NPC109744
0.6832 Remote Similarity NPC257510
0.6832 Remote Similarity NPC299714
0.6824 Remote Similarity NPC44122
0.6818 Remote Similarity NPC127094
0.6818 Remote Similarity NPC252182
0.6818 Remote Similarity NPC187471
0.6818 Remote Similarity NPC1340
0.6818 Remote Similarity NPC470071
0.6813 Remote Similarity NPC64081
0.6813 Remote Similarity NPC133596
0.6813 Remote Similarity NPC474574
0.6813 Remote Similarity NPC476233
0.6813 Remote Similarity NPC11907
0.6786 Remote Similarity NPC94897
0.6778 Remote Similarity NPC472950
0.6778 Remote Similarity NPC472952
0.6774 Remote Similarity NPC474714
0.6768 Remote Similarity NPC475751
0.6768 Remote Similarity NPC473956
0.6744 Remote Similarity NPC63190
0.6737 Remote Similarity NPC232023
0.6735 Remote Similarity NPC128475
0.6705 Remote Similarity NPC192192
0.6705 Remote Similarity NPC231945
0.6703 Remote Similarity NPC477601
0.6703 Remote Similarity NPC473916
0.6703 Remote Similarity NPC470145
0.6703 Remote Similarity NPC477602
0.6701 Remote Similarity NPC471240
0.6701 Remote Similarity NPC475276
0.67 Remote Similarity NPC293609
0.6667 Remote Similarity NPC236099
0.6667 Remote Similarity NPC249078
0.6667 Remote Similarity NPC209686
0.6634 Remote Similarity NPC277774
0.6633 Remote Similarity NPC263802
0.6633 Remote Similarity NPC161928
0.6633 Remote Similarity NPC474657
0.6633 Remote Similarity NPC472396
0.6633 Remote Similarity NPC210658
0.6633 Remote Similarity NPC186145
0.6632 Remote Similarity NPC470155
0.6632 Remote Similarity NPC477446
0.6632 Remote Similarity NPC477447
0.6629 Remote Similarity NPC157777
0.6629 Remote Similarity NPC131506
0.66 Remote Similarity NPC279329
0.6598 Remote Similarity NPC273290
0.6598 Remote Similarity NPC232044
0.6596 Remote Similarity NPC117137
0.6596 Remote Similarity NPC66766
0.6593 Remote Similarity NPC231680
0.6593 Remote Similarity NPC91387
0.6593 Remote Similarity NPC270306
0.6591 Remote Similarity NPC299948
0.6591 Remote Similarity NPC241085
0.6591 Remote Similarity NPC254037
0.6591 Remote Similarity NPC470830
0.6591 Remote Similarity NPC129829
0.6588 Remote Similarity NPC281540
0.6588 Remote Similarity NPC167995
0.6588 Remote Similarity NPC118937
0.6588 Remote Similarity NPC159654
0.6569 Remote Similarity NPC3538
0.6569 Remote Similarity NPC477224
0.6569 Remote Similarity NPC113500
0.6566 Remote Similarity NPC475664
0.6562 Remote Similarity NPC69953
0.6559 Remote Similarity NPC471769
0.6559 Remote Similarity NPC471045
0.6535 Remote Similarity NPC36372
0.6531 Remote Similarity NPC6605
0.6531 Remote Similarity NPC215968
0.6531 Remote Similarity NPC476726
0.6531 Remote Similarity NPC201273
0.6531 Remote Similarity NPC476727
0.6531 Remote Similarity NPC472272
0.6531 Remote Similarity NPC145245
0.6531 Remote Similarity NPC155531
0.6526 Remote Similarity NPC470156
0.6526 Remote Similarity NPC470154
0.6526 Remote Similarity NPC473257
0.6512 Remote Similarity NPC190827
0.6512 Remote Similarity NPC475943
0.6512 Remote Similarity NPC243469
0.6505 Remote Similarity NPC92196
0.65 Remote Similarity NPC20822
0.65 Remote Similarity NPC473472
0.6495 Remote Similarity NPC474156
0.6495 Remote Similarity NPC227260
0.6489 Remote Similarity NPC476176
0.6477 Remote Similarity NPC472741
0.6471 Remote Similarity NPC256104
0.6471 Remote Similarity NPC211845
0.6471 Remote Similarity NPC167644
0.6471 Remote Similarity NPC182740
0.6471 Remote Similarity NPC122083
0.6471 Remote Similarity NPC311246
0.6465 Remote Similarity NPC174273
0.6465 Remote Similarity NPC477600
0.6458 Remote Similarity NPC121121
0.6458 Remote Similarity NPC470611
0.6444 Remote Similarity NPC157422
0.6444 Remote Similarity NPC100586
0.6444 Remote Similarity NPC109457
0.6442 Remote Similarity NPC473287
0.6436 Remote Similarity NPC223143
0.6429 Remote Similarity NPC290612
0.6421 Remote Similarity NPC472943
0.6421 Remote Similarity NPC470609
0.6421 Remote Similarity NPC78545
0.6421 Remote Similarity NPC472951
0.6421 Remote Similarity NPC71535
0.6421 Remote Similarity NPC186588
0.6408 Remote Similarity NPC309866
0.6408 Remote Similarity NPC473503
0.6404 Remote Similarity NPC99264
0.64 Remote Similarity NPC131453
0.64 Remote Similarity NPC281004
0.64 Remote Similarity NPC473436
0.6392 Remote Similarity NPC477285
0.6392 Remote Similarity NPC111582
0.6392 Remote Similarity NPC29342
0.6392 Remote Similarity NPC241959
0.6392 Remote Similarity NPC2572
0.6392 Remote Similarity NPC470070
0.6386 Remote Similarity NPC47663
0.6383 Remote Similarity NPC31828
0.6383 Remote Similarity NPC477817
0.6383 Remote Similarity NPC477819
0.6381 Remote Similarity NPC477226
0.6381 Remote Similarity NPC477223
0.6381 Remote Similarity NPC477222

  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 NPC475817 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
0.6977 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6383 Remote Similarity NPD3671 Phase 1
0.6333 Remote Similarity NPD4787 Phase 1
0.6207 Remote Similarity NPD371 Approved
0.6082 Remote Similarity NPD6928 Phase 2
0.6042 Remote Similarity NPD6114 Approved
0.6042 Remote Similarity NPD6697 Approved
0.6042 Remote Similarity NPD6118 Approved
0.6042 Remote Similarity NPD6115 Approved
0.6 Remote Similarity NPD8171 Discontinued
0.5938 Remote Similarity NPD6116 Phase 1
0.5918 Remote Similarity NPD7525 Registered
0.5895 Remote Similarity NPD3703 Phase 2
0.5833 Remote Similarity NPD6117 Approved
0.5806 Remote Similarity NPD4245 Approved
0.5806 Remote Similarity NPD4244 Approved
0.5745 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5745 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7632 Discontinued
0.5699 Remote Similarity NPD3698 Phase 2
0.5699 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5699 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5673 Remote Similarity NPD7524 Approved
0.5625 Remote Similarity NPD6113 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