Structure

Physi-Chem Properties

Molecular Weight:  322.0
Volume:  254.588
LogP:  2.855
LogD:  3.228
LogS:  -3.446
# Rotatable Bonds:  1
TPSA:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.596
Synthetic Accessibility Score:  4.79
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.544
MDCK Permeability:  3.0447725293925032e-05
Pgp-inhibitor:  0.019
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.04
30% Bioavailability (F30%):  0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.977
Plasma Protein Binding (PPB):  93.17366790771484%
Volume Distribution (VD):  1.921
Pgp-substrate:  15.252815246582031%

ADMET: Metabolism

CYP1A2-inhibitor:  0.637
CYP1A2-substrate:  0.585
CYP2C19-inhibitor:  0.783
CYP2C19-substrate:  0.829
CYP2C9-inhibitor:  0.622
CYP2C9-substrate:  0.099
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.101
CYP3A4-inhibitor:  0.533
CYP3A4-substrate:  0.752

ADMET: Excretion

Clearance (CL):  6.507
Half-life (T1/2):  0.668

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.247
Drug-inuced Liver Injury (DILI):  0.078
AMES Toxicity:  0.229
Rat Oral Acute Toxicity:  0.813
Maximum Recommended Daily Dose:  0.926
Skin Sensitization:  0.593
Carcinogencity:  0.86
Eye Corrosion:  0.404
Eye Irritation:  0.654
Respiratory Toxicity:  0.95

Download Data

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

  Natural Product: NPC280810

Natural Product ID:  NPC280810
Common Name*:   Furocaespitanelactol
IUPAC Name:   (5S)-4-[(1R,3R,4R)-3-bromo-4-chloro-4-methylcyclohexyl]-5-hydroxy-5-methylfuran-2-one
Synonyms:   Furocaespitanelactol
Standard InCHIKey:  ARPGIRZFNMNODV-QNKRVWAESA-N
Standard InCHI:  InChI=1S/C12H16BrClO3/c1-11(14)4-3-7(5-9(11)13)8-6-10(15)17-12(8,2)16/h6-7,9,16H,3-5H2,1-2H3/t7-,9-,11-,12+/m1/s1
SMILES:  C[C@]1(CC[C@H](C[C@H]1Br)C1=CC(=O)O[C@]1(C)O)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1076862
PubChem CID:   46881072
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000267] Organohalogen compounds
      • [CHEMONTID:0002867] Alkyl halides
        • [CHEMONTID:0004485] Cyclohexyl halides

*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
NPO29486 Laurencia catarinensis Species Rhodomelaceae Eukaryota n.a. Brazilian n.a. PMID[20039643]
NPO29486 Laurencia catarinensis Species Rhodomelaceae 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
NPT139 Cell Line HT-29 Homo sapiens IC50 > 100000.0 nM PMID[448492]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 100000.0 nM PMID[448492]
NPT762 Cell Line A-431 Homo sapiens IC50 > 100000.0 nM PMID[448492]

☑ 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 NPC280810 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
0.9277 High Similarity NPC469570
0.9277 High Similarity NPC48210
0.7033 Intermediate Similarity NPC10636
0.6939 Remote Similarity NPC469538
0.6915 Remote Similarity NPC474693
0.6842 Remote Similarity NPC475860
0.6842 Remote Similarity NPC473251
0.6842 Remote Similarity NPC474694
0.6842 Remote Similarity NPC42586
0.6842 Remote Similarity NPC473659
0.6782 Remote Similarity NPC316029
0.6742 Remote Similarity NPC77724
0.6737 Remote Similarity NPC471302
0.6735 Remote Similarity NPC470734
0.6702 Remote Similarity NPC471298
0.6633 Remote Similarity NPC472809
0.6633 Remote Similarity NPC472810
0.6632 Remote Similarity NPC311070
0.6632 Remote Similarity NPC471297
0.6628 Remote Similarity NPC472266
0.66 Remote Similarity NPC289479
0.66 Remote Similarity NPC329842
0.6562 Remote Similarity NPC282598
0.6562 Remote Similarity NPC471301
0.6559 Remote Similarity NPC477088
0.6552 Remote Similarity NPC313444
0.6535 Remote Similarity NPC472303
0.6522 Remote Similarity NPC315394
0.6522 Remote Similarity NPC473756
0.65 Remote Similarity NPC281942
0.65 Remote Similarity NPC232426
0.6495 Remote Similarity NPC287015
0.6495 Remote Similarity NPC146850
0.6495 Remote Similarity NPC471795
0.6477 Remote Similarity NPC265574
0.6477 Remote Similarity NPC232812
0.6471 Remote Similarity NPC298973
0.6471 Remote Similarity NPC469697
0.6471 Remote Similarity NPC104925
0.6465 Remote Similarity NPC474629
0.6465 Remote Similarity NPC242448
0.6465 Remote Similarity NPC472378
0.6458 Remote Similarity NPC472377
0.6458 Remote Similarity NPC42476
0.6436 Remote Similarity NPC472811
0.6436 Remote Similarity NPC477122
0.6436 Remote Similarity NPC141831
0.6429 Remote Similarity NPC471219
0.6421 Remote Similarity NPC475944
0.6421 Remote Similarity NPC78677
0.6421 Remote Similarity NPC59994
0.6408 Remote Similarity NPC472441
0.6404 Remote Similarity NPC64234
0.6404 Remote Similarity NPC67183
0.6404 Remote Similarity NPC315597
0.6404 Remote Similarity NPC4299
0.6404 Remote Similarity NPC37929
0.6373 Remote Similarity NPC472812
0.6364 Remote Similarity NPC471796
0.6364 Remote Similarity NPC312561
0.6354 Remote Similarity NPC215175
0.6354 Remote Similarity NPC323251
0.6346 Remote Similarity NPC162346
0.6344 Remote Similarity NPC54996
0.6344 Remote Similarity NPC316324
0.6344 Remote Similarity NPC262747
0.6337 Remote Similarity NPC477782
0.6337 Remote Similarity NPC78973
0.6327 Remote Similarity NPC147921
0.6327 Remote Similarity NPC471494
0.6327 Remote Similarity NPC472442
0.6327 Remote Similarity NPC253604
0.6322 Remote Similarity NPC116013
0.6321 Remote Similarity NPC472012
0.6311 Remote Similarity NPC324078
0.6311 Remote Similarity NPC470255
0.6304 Remote Similarity NPC329852
0.6292 Remote Similarity NPC101622
0.6289 Remote Similarity NPC474809
0.6289 Remote Similarity NPC30502
0.6289 Remote Similarity NPC472440
0.6286 Remote Similarity NPC477718
0.6286 Remote Similarity NPC477719
0.6286 Remote Similarity NPC476253
0.6277 Remote Similarity NPC209135
0.6277 Remote Similarity NPC474816
0.6277 Remote Similarity NPC184737
0.6277 Remote Similarity NPC172066
0.6275 Remote Similarity NPC477783
0.6263 Remote Similarity NPC474062
0.6263 Remote Similarity NPC311163
0.6263 Remote Similarity NPC131813
0.625 Remote Similarity NPC325031
0.6238 Remote Similarity NPC5509
0.6238 Remote Similarity NPC251528
0.6237 Remote Similarity NPC469880
0.6237 Remote Similarity NPC30575
0.6224 Remote Similarity NPC126518
0.6224 Remote Similarity NPC470800
0.6222 Remote Similarity NPC315285
0.6214 Remote Similarity NPC156553
0.6214 Remote Similarity NPC115021
0.6211 Remote Similarity NPC242767
0.6211 Remote Similarity NPC469617
0.6211 Remote Similarity NPC476603
0.62 Remote Similarity NPC475678
0.62 Remote Similarity NPC316138
0.62 Remote Similarity NPC313658
0.619 Remote Similarity NPC470801
0.619 Remote Similarity NPC165632
0.6186 Remote Similarity NPC324170
0.6186 Remote Similarity NPC471296
0.6186 Remote Similarity NPC471218
0.618 Remote Similarity NPC276290
0.6176 Remote Similarity NPC182136
0.617 Remote Similarity NPC189206
0.617 Remote Similarity NPC132542
0.617 Remote Similarity NPC476439
0.6168 Remote Similarity NPC477721
0.6168 Remote Similarity NPC472826
0.6168 Remote Similarity NPC324841
0.6168 Remote Similarity NPC476767
0.6168 Remote Similarity NPC477716
0.6162 Remote Similarity NPC471300
0.6162 Remote Similarity NPC65661
0.6162 Remote Similarity NPC30984
0.6162 Remote Similarity NPC329630
0.6162 Remote Similarity NPC474860
0.6162 Remote Similarity NPC86316
0.6162 Remote Similarity NPC106416
0.6162 Remote Similarity NPC163606
0.6161 Remote Similarity NPC322912
0.6154 Remote Similarity NPC472254
0.6146 Remote Similarity NPC15714
0.6136 Remote Similarity NPC81907
0.6136 Remote Similarity NPC315115
0.6132 Remote Similarity NPC475709
0.6129 Remote Similarity NPC265921
0.6129 Remote Similarity NPC85831
0.6129 Remote Similarity NPC215215
0.6126 Remote Similarity NPC319438
0.6126 Remote Similarity NPC216636
0.6122 Remote Similarity NPC321385
0.6122 Remote Similarity NPC477124
0.6122 Remote Similarity NPC476927
0.6117 Remote Similarity NPC472814
0.6117 Remote Similarity NPC177037
0.6111 Remote Similarity NPC151481
0.6111 Remote Similarity NPC477717
0.6111 Remote Similarity NPC475004
0.6105 Remote Similarity NPC471220
0.6105 Remote Similarity NPC93763
0.6105 Remote Similarity NPC108816
0.6087 Remote Similarity NPC476489
0.6087 Remote Similarity NPC477085
0.6087 Remote Similarity NPC476490
0.6082 Remote Similarity NPC112868
0.6078 Remote Similarity NPC474396
0.6078 Remote Similarity NPC225283
0.6078 Remote Similarity NPC174342
0.6078 Remote Similarity NPC50488
0.6064 Remote Similarity NPC476317
0.6061 Remote Similarity NPC290052
0.6061 Remote Similarity NPC30486
0.6061 Remote Similarity NPC82297
0.6061 Remote Similarity NPC475706
0.6058 Remote Similarity NPC166346
0.6058 Remote Similarity NPC7349
0.6058 Remote Similarity NPC53555
0.6058 Remote Similarity NPC59646
0.6055 Remote Similarity NPC472815
0.6042 Remote Similarity NPC110373
0.6042 Remote Similarity NPC55304
0.6042 Remote Similarity NPC80471
0.6042 Remote Similarity NPC31330
0.6042 Remote Similarity NPC139712
0.6042 Remote Similarity NPC5908
0.6042 Remote Similarity NPC226226
0.6042 Remote Similarity NPC89128
0.604 Remote Similarity NPC473891
0.6023 Remote Similarity NPC475110
0.6023 Remote Similarity NPC470688
0.6022 Remote Similarity NPC470686
0.602 Remote Similarity NPC256112
0.6019 Remote Similarity NPC477720
0.6019 Remote Similarity NPC51486
0.6019 Remote Similarity NPC310479
0.6019 Remote Similarity NPC3436
0.6019 Remote Similarity NPC472644
0.6019 Remote Similarity NPC221111
0.6019 Remote Similarity NPC472642
0.6019 Remote Similarity NPC280149
0.6019 Remote Similarity NPC16601
0.6 Remote Similarity NPC67081
0.6 Remote Similarity NPC105490
0.6 Remote Similarity NPC320630
0.6 Remote Similarity NPC470521
0.6 Remote Similarity NPC474554
0.6 Remote Similarity NPC84360
0.6 Remote Similarity NPC40049

  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 NPC280810 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
0.6224 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6023 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5909 Remote Similarity NPD7632 Discontinued
0.5888 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5859 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5727 Remote Similarity NPD7639 Approved
0.5727 Remote Similarity NPD7640 Approved
0.5686 Remote Similarity NPD1694 Approved
0.5636 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5636 Remote Similarity NPD4225 Approved
0.5636 Remote Similarity NPD7638 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