Structure

Physi-Chem Properties

Molecular Weight:  1183.43
Volume:  722.593
LogP:  8.052
LogD:  2.474
LogS:  -9.003
# Rotatable Bonds:  12
TPSA:  164.12
# H-Bond Aceptor:  12
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.114
Synthetic Accessibility Score:  3.379
Fsp3:  0.0
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.913
MDCK Permeability:  1.0711080904002301e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  1.0
20% Bioavailability (F20%):  0.426
30% Bioavailability (F30%):  0.407

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  124.78595733642578%
Volume Distribution (VD):  -0.118
Pgp-substrate:  5.521621227264404%

ADMET: Metabolism

CYP1A2-inhibitor:  0.477
CYP1A2-substrate:  0.132
CYP2C19-inhibitor:  0.718
CYP2C19-substrate:  0.088
CYP2C9-inhibitor:  0.901
CYP2C9-substrate:  0.962
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.799
CYP3A4-inhibitor:  0.027
CYP3A4-substrate:  0.116

ADMET: Excretion

Clearance (CL):  0.194
Half-life (T1/2):  0.003

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.036
Drug-inuced Liver Injury (DILI):  0.064
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.989
Maximum Recommended Daily Dose:  0.979
Skin Sensitization:  0.943
Carcinogencity:  0.669
Eye Corrosion:  0.003
Eye Irritation:  0.891
Respiratory Toxicity:  0.67

Download Data

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

  Natural Product: NPC286337

Natural Product ID:  NPC286337
Common Name*:   Crossbyanol B
IUPAC Name:   [2-bromo-4-[3-bromo-4-[2-bromo-3-(2,4-dibromophenoxy)-4-sulfooxyphenoxy]-5-(2,4-dibromophenoxy)phenoxy]phenyl] hydrogen sulfate
Synonyms:  
Standard InCHIKey:  PGLDWZUFBSDOEM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C30H15Br7O12S2/c31-14-1-4-22(18(33)9-14)45-27-13-17(44-16-3-6-24(20(35)11-16)48-50(38,39)40)12-21(36)29(27)47-25-7-8-26(49-51(41,42)43)30(28(25)37)46-23-5-2-15(32)10-19(23)34/h1-13H,(H,38,39,40)(H,41,42,43)
SMILES:  Brc1ccc(c(c1)Br)Oc1cc(Oc2ccc(c(c2)Br)OS(=O)(=O)O)cc(c1Oc1ccc(c(c1Br)Oc1ccc(cc1Br)Br)OS(=O)(=O)O)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1097913
PubChem CID:   46211029
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0004155] Diphenylethers
          • [CHEMONTID:0001845] Bromodiphenyl ethers

*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
NPO32575 leptolyngbya crossbyana Species Leptolyngbyaceae Bacteria n.a. Hawai'ian bloom-forming Cyanobacterium n.a. PMID[20170122]

☑ 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 2.0 ug.mL-1 PMID[556083]
NPT176 Organism Artemia salina Artemia salina IC50 = 2.8 ppm PMID[556083]

☑ 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 NPC286337 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
0.9137 High Similarity NPC8577
0.8162 Intermediate Similarity NPC235166
0.8116 Intermediate Similarity NPC163019
0.8116 Intermediate Similarity NPC1744
0.8 Intermediate Similarity NPC45728
0.7958 Intermediate Similarity NPC222684
0.7958 Intermediate Similarity NPC206183
0.7902 Intermediate Similarity NPC178301
0.7778 Intermediate Similarity NPC162294
0.7704 Intermediate Similarity NPC221301
0.7591 Intermediate Similarity NPC264379
0.7589 Intermediate Similarity NPC105147
0.7589 Intermediate Similarity NPC228875
0.7589 Intermediate Similarity NPC126216
0.7554 Intermediate Similarity NPC44270
0.7554 Intermediate Similarity NPC86007
0.75 Intermediate Similarity NPC110677
0.7482 Intermediate Similarity NPC71186
0.7482 Intermediate Similarity NPC104124
0.7447 Intermediate Similarity NPC153580
0.7447 Intermediate Similarity NPC205850
0.7447 Intermediate Similarity NPC47769
0.7447 Intermediate Similarity NPC170824
0.7447 Intermediate Similarity NPC299939
0.7447 Intermediate Similarity NPC196371
0.7447 Intermediate Similarity NPC226737
0.7429 Intermediate Similarity NPC214289
0.741 Intermediate Similarity NPC151617
0.741 Intermediate Similarity NPC76915
0.7376 Intermediate Similarity NPC63317
0.7376 Intermediate Similarity NPC41232
0.7343 Intermediate Similarity NPC295879
0.7343 Intermediate Similarity NPC64130
0.7343 Intermediate Similarity NPC175520
0.7343 Intermediate Similarity NPC97157
0.7343 Intermediate Similarity NPC159866
0.7343 Intermediate Similarity NPC25134
0.7273 Intermediate Similarity NPC137922
0.7273 Intermediate Similarity NPC40302
0.7273 Intermediate Similarity NPC173511
0.7273 Intermediate Similarity NPC474375
0.7273 Intermediate Similarity NPC88733
0.7234 Intermediate Similarity NPC191194
0.7172 Intermediate Similarity NPC68350
0.7172 Intermediate Similarity NPC197576
0.7172 Intermediate Similarity NPC81149
0.7172 Intermediate Similarity NPC131940
0.7172 Intermediate Similarity NPC230013
0.7143 Intermediate Similarity NPC319933
0.6821 Remote Similarity NPC247146
0.681 Remote Similarity NPC152947
0.6752 Remote Similarity NPC48956
0.672 Remote Similarity NPC156055
0.6667 Remote Similarity NPC474227
0.6667 Remote Similarity NPC25817
0.6667 Remote Similarity NPC262189
0.6645 Remote Similarity NPC131128
0.6645 Remote Similarity NPC474134
0.6626 Remote Similarity NPC95652
0.6626 Remote Similarity NPC150714
0.6619 Remote Similarity NPC232654
0.66 Remote Similarity NPC217854
0.6591 Remote Similarity NPC475615
0.6581 Remote Similarity NPC474238
0.6579 Remote Similarity NPC298845
0.6576 Remote Similarity NPC469721
0.6561 Remote Similarity NPC66840
0.6561 Remote Similarity NPC256307
0.6545 Remote Similarity NPC281549
0.6541 Remote Similarity NPC474390
0.6536 Remote Similarity NPC37074
0.6516 Remote Similarity NPC60756
0.651 Remote Similarity NPC276195
0.6506 Remote Similarity NPC476969
0.6505 Remote Similarity NPC469731
0.6503 Remote Similarity NPC171932
0.6503 Remote Similarity NPC28440
0.6497 Remote Similarity NPC60982
0.6474 Remote Similarity NPC287780
0.6471 Remote Similarity NPC469622
0.6471 Remote Similarity NPC189589
0.646 Remote Similarity NPC61783
0.646 Remote Similarity NPC20520
0.646 Remote Similarity NPC22317
0.6454 Remote Similarity NPC124712
0.6447 Remote Similarity NPC221090
0.6429 Remote Similarity NPC144823
0.6424 Remote Similarity NPC152722
0.641 Remote Similarity NPC477804
0.641 Remote Similarity NPC208769
0.641 Remote Similarity NPC229231
0.64 Remote Similarity NPC472596
0.6398 Remote Similarity NPC55947
0.6382 Remote Similarity NPC192810
0.6364 Remote Similarity NPC171533
0.6352 Remote Similarity NPC474600
0.6352 Remote Similarity NPC310854
0.6348 Remote Similarity NPC469979
0.6339 Remote Similarity NPC471591
0.6339 Remote Similarity NPC473892
0.6339 Remote Similarity NPC475658
0.6329 Remote Similarity NPC161203
0.6323 Remote Similarity NPC469621
0.6323 Remote Similarity NPC216836
0.6316 Remote Similarity NPC261661
0.6313 Remote Similarity NPC473462
0.6313 Remote Similarity NPC110454
0.6313 Remote Similarity NPC207819
0.6313 Remote Similarity NPC126128
0.6313 Remote Similarity NPC298981
0.6312 Remote Similarity NPC307875
0.6312 Remote Similarity NPC195022
0.631 Remote Similarity NPC211561
0.6309 Remote Similarity NPC228907
0.6306 Remote Similarity NPC214860
0.6304 Remote Similarity NPC141405
0.6304 Remote Similarity NPC473409
0.6304 Remote Similarity NPC82741
0.6301 Remote Similarity NPC36077
0.6296 Remote Similarity NPC22517
0.6289 Remote Similarity NPC37196
0.6289 Remote Similarity NPC94236
0.6289 Remote Similarity NPC269528
0.6287 Remote Similarity NPC262911
0.6287 Remote Similarity NPC294558
0.6287 Remote Similarity NPC108811
0.6287 Remote Similarity NPC236202
0.6287 Remote Similarity NPC202742
0.6287 Remote Similarity NPC204770
0.6287 Remote Similarity NPC82917
0.6287 Remote Similarity NPC70409
0.6287 Remote Similarity NPC18185
0.6287 Remote Similarity NPC58190
0.6287 Remote Similarity NPC263940
0.6287 Remote Similarity NPC170103
0.6284 Remote Similarity NPC123948
0.6282 Remote Similarity NPC63179
0.6282 Remote Similarity NPC31707
0.628 Remote Similarity NPC477800
0.628 Remote Similarity NPC477794
0.628 Remote Similarity NPC477799
0.6273 Remote Similarity NPC173660
0.6272 Remote Similarity NPC477612
0.6266 Remote Similarity NPC473412
0.6266 Remote Similarity NPC469698
0.6266 Remote Similarity NPC469613
0.6266 Remote Similarity NPC30043
0.6266 Remote Similarity NPC469625
0.6265 Remote Similarity NPC125617
0.6264 Remote Similarity NPC36354
0.6258 Remote Similarity NPC291101
0.6258 Remote Similarity NPC244364
0.6258 Remote Similarity NPC266197
0.6257 Remote Similarity NPC226001
0.625 Remote Similarity NPC245386
0.625 Remote Similarity NPC106215
0.625 Remote Similarity NPC227516
0.625 Remote Similarity NPC474478
0.625 Remote Similarity NPC145780
0.625 Remote Similarity NPC170694
0.625 Remote Similarity NPC20757
0.6243 Remote Similarity NPC475396
0.6242 Remote Similarity NPC285339
0.6242 Remote Similarity NPC210623
0.6242 Remote Similarity NPC210655
0.6242 Remote Similarity NPC202582
0.6242 Remote Similarity NPC190629
0.6242 Remote Similarity NPC222004
0.6242 Remote Similarity NPC45824
0.6242 Remote Similarity NPC218856
0.6242 Remote Similarity NPC273295
0.6242 Remote Similarity NPC470258
0.6242 Remote Similarity NPC3439
0.6242 Remote Similarity NPC226788
0.6235 Remote Similarity NPC474282
0.6235 Remote Similarity NPC326797
0.6235 Remote Similarity NPC107551
0.6235 Remote Similarity NPC176051
0.6235 Remote Similarity NPC276490
0.6235 Remote Similarity NPC102904
0.6235 Remote Similarity NPC103976
0.6235 Remote Similarity NPC271942
0.6234 Remote Similarity NPC122792
0.6234 Remote Similarity NPC228972
0.6228 Remote Similarity NPC113862
0.6228 Remote Similarity NPC96576
0.6226 Remote Similarity NPC202762
0.6226 Remote Similarity NPC86655
0.6226 Remote Similarity NPC35932
0.6226 Remote Similarity NPC184447
0.6226 Remote Similarity NPC16208
0.6226 Remote Similarity NPC7903
0.6226 Remote Similarity NPC160991
0.6221 Remote Similarity NPC157333
0.622 Remote Similarity NPC118794
0.622 Remote Similarity NPC100482
0.622 Remote Similarity NPC178054
0.622 Remote Similarity NPC277331
0.6218 Remote Similarity NPC210355
0.6218 Remote Similarity NPC50368

  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 NPC286337 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
0.6185 Remote Similarity NPD4288 Approved
0.6178 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6178 Remote Similarity NPD8095 Phase 1
0.6178 Remote Similarity NPD3537 Clinical (unspecified phase)
0.6169 Remote Similarity NPD2982 Phase 2
0.6169 Remote Similarity NPD2983 Phase 2
0.6135 Remote Similarity NPD3454 Phase 3
0.6133 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6115 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6104 Remote Similarity NPD2981 Phase 2
0.6099 Remote Similarity NPD291 Approved
0.6093 Remote Similarity NPD7533 Approved
0.6093 Remote Similarity NPD7534 Approved
0.6025 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6025 Remote Similarity NPD1613 Approved
0.6013 Remote Similarity NPD3018 Phase 2
0.5975 Remote Similarity NPD4908 Phase 1
0.5938 Remote Similarity NPD3027 Phase 3
0.5926 Remote Similarity NPD4287 Approved
0.5901 Remote Similarity NPD4907 Clinical (unspecified phase)
0.5882 Remote Similarity NPD1548 Phase 1
0.5811 Remote Similarity NPD556 Approved
0.5808 Remote Similarity NPD3540 Phase 1
0.5797 Remote Similarity NPD9365 Approved
0.575 Remote Similarity NPD1469 Clinical (unspecified phase)
0.5749 Remote Similarity NPD3539 Phase 1
0.5732 Remote Similarity NPD1610 Phase 2
0.5714 Remote Similarity NPD968 Approved
0.5674 Remote Similarity NPD2801 Approved
0.5674 Remote Similarity NPD9296 Approved
0.5657 Remote Similarity NPD1653 Approved
0.5652 Remote Similarity NPD6166 Phase 2
0.5652 Remote Similarity NPD6168 Clinical (unspecified phase)
0.5652 Remote Similarity NPD6167 Clinical (unspecified phase)
0.5632 Remote Similarity NPD1940 Clinical (unspecified phase)
0.5625 Remote Similarity NPD6055 Clinical (unspecified phase)
0.5611 Remote Similarity NPD4868 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