Structure

Physi-Chem Properties

Molecular Weight:  336.01
Volume:  271.884
LogP:  3.586
LogD:  3.045
LogS:  -4.104
# Rotatable Bonds:  2
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.572
Synthetic Accessibility Score:  4.838
Fsp3:  0.769
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.518
MDCK Permeability:  2.4787039365037344e-05
Pgp-inhibitor:  0.923
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.053
30% Bioavailability (F30%):  0.323

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.946
Plasma Protein Binding (PPB):  96.03287506103516%
Volume Distribution (VD):  2.085
Pgp-substrate:  6.7505292892456055%

ADMET: Metabolism

CYP1A2-inhibitor:  0.682
CYP1A2-substrate:  0.817
CYP2C19-inhibitor:  0.838
CYP2C19-substrate:  0.903
CYP2C9-inhibitor:  0.798
CYP2C9-substrate:  0.078
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.185
CYP3A4-inhibitor:  0.63
CYP3A4-substrate:  0.864

ADMET: Excretion

Clearance (CL):  5.365
Half-life (T1/2):  0.711

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.381
Drug-inuced Liver Injury (DILI):  0.235
AMES Toxicity:  0.467
Rat Oral Acute Toxicity:  0.14
Maximum Recommended Daily Dose:  0.428
Skin Sensitization:  0.407
Carcinogencity:  0.867
Eye Corrosion:  0.149
Eye Irritation:  0.284
Respiratory Toxicity:  0.856

Download Data

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

  Natural Product: NPC48210

Natural Product ID:  NPC48210
Common Name*:   (10R*)-10-O-Methylfurocaespitanelactol
IUPAC Name:   (5R)-4-[(1R,3R,4R)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methoxy-5-methylfuran-2-one
Synonyms:  
Standard InCHIKey:  HZRBFPFRPXJJQB-PIEOMLNGSA-N
Standard InCHI:  InChI=1S/C13H18BrClO3/c1-12(15)5-4-8(6-10(12)14)9-7-11(16)18-13(9,2)17-3/h7-8,10H,4-6H2,1-3H3/t8-,10-,12-,13-/m1/s1
SMILES:  CO[C@]1(C)OC(=O)C=C1[C@@H]1CC[C@@]([C@@H](C1)Br)(C)Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1088456
PubChem CID:   44626955
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[448459]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 100000.0 nM PMID[448459]
NPT762 Cell Line A-431 Homo sapiens IC50 > 100000.0 nM PMID[448459]

☑ 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 NPC48210 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
1.0 High Similarity NPC469570
0.9277 High Similarity NPC280810
0.7093 Intermediate Similarity NPC77724
0.7083 Intermediate Similarity NPC469538
0.6988 Remote Similarity NPC472266
0.6882 Remote Similarity NPC282598
0.6824 Remote Similarity NPC232812
0.6809 Remote Similarity NPC472442
0.6774 Remote Similarity NPC30502
0.6774 Remote Similarity NPC472440
0.6744 Remote Similarity NPC37929
0.6744 Remote Similarity NPC64234
0.6628 Remote Similarity NPC265574
0.6593 Remote Similarity NPC184737
0.6591 Remote Similarity NPC476490
0.6591 Remote Similarity NPC476489
0.6548 Remote Similarity NPC475110
0.6512 Remote Similarity NPC276290
0.6489 Remote Similarity NPC471218
0.6484 Remote Similarity NPC189206
0.6484 Remote Similarity NPC54996
0.6471 Remote Similarity NPC116013
0.6458 Remote Similarity NPC473251
0.6458 Remote Similarity NPC42586
0.6452 Remote Similarity NPC10636
0.6452 Remote Similarity NPC15714
0.6413 Remote Similarity NPC471220
0.6364 Remote Similarity NPC316029
0.6364 Remote Similarity NPC470734
0.6354 Remote Similarity NPC474693
0.6354 Remote Similarity NPC30486
0.6354 Remote Similarity NPC471302
0.6344 Remote Similarity NPC477088
0.6316 Remote Similarity NPC471298
0.6304 Remote Similarity NPC187568
0.6304 Remote Similarity NPC41780
0.6289 Remote Similarity NPC473659
0.6289 Remote Similarity NPC474013
0.6289 Remote Similarity NPC471795
0.6289 Remote Similarity NPC475860
0.6289 Remote Similarity NPC189311
0.6289 Remote Similarity NPC474694
0.6279 Remote Similarity NPC191233
0.6277 Remote Similarity NPC268827
0.6275 Remote Similarity NPC477722
0.6265 Remote Similarity NPC19241
0.6263 Remote Similarity NPC472809
0.6263 Remote Similarity NPC472378
0.6263 Remote Similarity NPC76909
0.6263 Remote Similarity NPC472810
0.625 Remote Similarity NPC193198
0.625 Remote Similarity NPC471297
0.625 Remote Similarity NPC311070
0.625 Remote Similarity NPC477124
0.6238 Remote Similarity NPC329842
0.6238 Remote Similarity NPC141831
0.6237 Remote Similarity NPC128276
0.6237 Remote Similarity NPC299235
0.6224 Remote Similarity NPC471219
0.6224 Remote Similarity NPC477428
0.6222 Remote Similarity NPC222244
0.6222 Remote Similarity NPC16349
0.6196 Remote Similarity NPC40353
0.6196 Remote Similarity NPC473223
0.6186 Remote Similarity NPC96055
0.6186 Remote Similarity NPC71626
0.6186 Remote Similarity NPC475100
0.6186 Remote Similarity NPC318515
0.6186 Remote Similarity NPC471301
0.6186 Remote Similarity NPC149869
0.618 Remote Similarity NPC475113
0.618 Remote Similarity NPC469660
0.618 Remote Similarity NPC299932
0.6176 Remote Similarity NPC156553
0.6176 Remote Similarity NPC472303
0.617 Remote Similarity NPC150646
0.6163 Remote Similarity NPC220766
0.6163 Remote Similarity NPC470688
0.6162 Remote Similarity NPC471796
0.6154 Remote Similarity NPC294434
0.6154 Remote Similarity NPC474758
0.6154 Remote Similarity NPC259599
0.6154 Remote Similarity NPC33876
0.6154 Remote Similarity NPC277993
0.6154 Remote Similarity NPC117746
0.6154 Remote Similarity NPC15499
0.6146 Remote Similarity NPC200513
0.6139 Remote Similarity NPC281942
0.6139 Remote Similarity NPC232426
0.6136 Remote Similarity NPC477431
0.6136 Remote Similarity NPC313444
0.6132 Remote Similarity NPC472012
0.6129 Remote Similarity NPC57744
0.6129 Remote Similarity NPC473756
0.6129 Remote Similarity NPC315394
0.6129 Remote Similarity NPC471225
0.6129 Remote Similarity NPC316500
0.6118 Remote Similarity NPC217940
0.6117 Remote Similarity NPC469697
0.6117 Remote Similarity NPC104925
0.6117 Remote Similarity NPC298973
0.6111 Remote Similarity NPC257618
0.6111 Remote Similarity NPC269103
0.6111 Remote Similarity NPC124072
0.61 Remote Similarity NPC474629
0.61 Remote Similarity NPC226863
0.61 Remote Similarity NPC472302
0.61 Remote Similarity NPC93411
0.6095 Remote Similarity NPC476768
0.6087 Remote Similarity NPC329852
0.6082 Remote Similarity NPC474193
0.6082 Remote Similarity NPC12283
0.6082 Remote Similarity NPC472377
0.6082 Remote Similarity NPC42476
0.6082 Remote Similarity NPC22611
0.6078 Remote Similarity NPC472811
0.6078 Remote Similarity NPC289479
0.6078 Remote Similarity NPC477122
0.6078 Remote Similarity NPC65513
0.6067 Remote Similarity NPC101622
0.6067 Remote Similarity NPC269841
0.6067 Remote Similarity NPC470693
0.6061 Remote Similarity NPC118266
0.6061 Remote Similarity NPC131813
0.6058 Remote Similarity NPC472441
0.6042 Remote Similarity NPC475944
0.6042 Remote Similarity NPC282293
0.6042 Remote Similarity NPC471325
0.604 Remote Similarity NPC5509
0.604 Remote Similarity NPC251528
0.604 Remote Similarity NPC293044
0.604 Remote Similarity NPC242877
0.604 Remote Similarity NPC64913
0.6022 Remote Similarity NPC469581
0.6022 Remote Similarity NPC469880
0.6022 Remote Similarity NPC27205
0.6022 Remote Similarity NPC123360
0.6022 Remote Similarity NPC235906
0.6019 Remote Similarity NPC472812
0.6 Remote Similarity NPC323677
0.6 Remote Similarity NPC477429
0.6 Remote Similarity NPC178277
0.6 Remote Similarity NPC477423
0.6 Remote Similarity NPC312561
0.6 Remote Similarity NPC325960
0.6 Remote Similarity NPC162346
0.6 Remote Similarity NPC316138
0.6 Remote Similarity NPC313658
0.6 Remote Similarity NPC319692
0.6 Remote Similarity NPC4299
0.6 Remote Similarity NPC315285
0.6 Remote Similarity NPC475678
0.6 Remote Similarity NPC67183
0.6 Remote Similarity NPC242767
0.6 Remote Similarity NPC112654
0.5981 Remote Similarity NPC477721
0.5981 Remote Similarity NPC477716
0.598 Remote Similarity NPC78973
0.598 Remote Similarity NPC8062
0.598 Remote Similarity NPC477782
0.5979 Remote Similarity NPC35556
0.5979 Remote Similarity NPC323251
0.5979 Remote Similarity NPC215175
0.5979 Remote Similarity NPC173609
0.5979 Remote Similarity NPC186276
0.5978 Remote Similarity NPC188354
0.5978 Remote Similarity NPC476355
0.5977 Remote Similarity NPC182794
0.5976 Remote Similarity NPC141699
0.5976 Remote Similarity NPC96663
0.5962 Remote Similarity NPC470255
0.5962 Remote Similarity NPC324078
0.596 Remote Similarity NPC30984
0.596 Remote Similarity NPC65661
0.596 Remote Similarity NPC471494
0.596 Remote Similarity NPC177932
0.596 Remote Similarity NPC106416
0.596 Remote Similarity NPC146850
0.596 Remote Similarity NPC163606
0.596 Remote Similarity NPC86316
0.596 Remote Similarity NPC287015
0.5957 Remote Similarity NPC262747
0.5957 Remote Similarity NPC316324
0.5957 Remote Similarity NPC65603
0.5957 Remote Similarity NPC10572
0.5955 Remote Similarity NPC218477
0.5946 Remote Similarity NPC216636
0.5946 Remote Similarity NPC319438
0.5943 Remote Similarity NPC477719
0.5943 Remote Similarity NPC477718
0.5941 Remote Similarity NPC196407
0.5941 Remote Similarity NPC242448
0.5938 Remote Similarity NPC195424
0.5938 Remote Similarity NPC47747
0.5938 Remote Similarity NPC233332
0.5934 Remote Similarity NPC163003
0.5934 Remote Similarity NPC477084
0.5934 Remote Similarity NPC129665
0.5926 Remote Similarity NPC477717
0.5922 Remote Similarity NPC477783

  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 NPC48210 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
0.6353 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6146 Remote Similarity NPD4752 Clinical (unspecified phase)
0.596 Remote Similarity NPD1694 Approved
0.5859 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5698 Remote Similarity NPD1145 Discontinued

  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