Structure

Physi-Chem Properties

Molecular Weight:  1023.52
Volume:  632.834
LogP:  9.542
LogD:  3.176
LogS:  -10.618
# Rotatable Bonds:  8
TPSA:  77.38
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.161
Synthetic Accessibility Score:  3.079
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:  -6.271
MDCK Permeability:  1.1141059985675383e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.998
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.149

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.091
Plasma Protein Binding (PPB):  118.92607879638672%
Volume Distribution (VD):  0.45
Pgp-substrate:  12.269168853759766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.649
CYP1A2-substrate:  0.104
CYP2C19-inhibitor:  0.728
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.685
CYP2C9-substrate:  0.938
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.91
CYP3A4-inhibitor:  0.048
CYP3A4-substrate:  0.155

ADMET: Excretion

Clearance (CL):  -0.172
Half-life (T1/2):  0.033

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.021
Drug-inuced Liver Injury (DILI):  0.954
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.995
Maximum Recommended Daily Dose:  0.954
Skin Sensitization:  0.948
Carcinogencity:  0.051
Eye Corrosion:  0.003
Eye Irritation:  0.941
Respiratory Toxicity:  0.424

Download Data

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

  Natural Product: NPC8577

Natural Product ID:  NPC8577
Common Name*:   Crossbyanol A
IUPAC Name:   3-bromo-4-[2-bromo-4-(3-bromo-4-hydroxyphenoxy)-6-(2,4-dibromophenoxy)phenoxy]-2-(2,4-dibromophenoxy)phenol
Synonyms:  
Standard InCHIKey:  NBQGOUOMJQLWCZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C30H15Br7O6/c31-14-1-6-24(19(34)9-14)41-27-13-17(40-16-3-4-22(38)18(33)11-16)12-21(36)29(27)43-26-8-5-23(39)30(28(26)37)42-25-7-2-15(32)10-20(25)35/h1-13,38-39H
SMILES:  Brc1ccc(c(c1)Br)Oc1cc(Oc2ccc(c(c2)Br)O)cc(c1Oc1ccc(c(c1Br)Oc1ccc(cc1Br)Br)O)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1097912
PubChem CID:   46210880
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
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 30.0 ug.mL-1 PMID[555323]
NPT2 Others Unspecified IC50 = 20.0 ug.mL-1 PMID[555323]

☑ 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 NPC8577 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 NPC286337
0.8806 High Similarity NPC45728
0.875 High Similarity NPC222684
0.875 High Similarity NPC206183
0.8686 High Similarity NPC178301
0.8346 Intermediate Similarity NPC86007
0.8346 Intermediate Similarity NPC44270
0.8271 Intermediate Similarity NPC104124
0.8235 Intermediate Similarity NPC228875
0.8235 Intermediate Similarity NPC105147
0.8235 Intermediate Similarity NPC126216
0.8222 Intermediate Similarity NPC226737
0.8222 Intermediate Similarity NPC299939
0.8222 Intermediate Similarity NPC196371
0.8222 Intermediate Similarity NPC47769
0.8222 Intermediate Similarity NPC170824
0.8222 Intermediate Similarity NPC153580
0.8162 Intermediate Similarity NPC235166
0.8148 Intermediate Similarity NPC41232
0.8148 Intermediate Similarity NPC63317
0.8129 Intermediate Similarity NPC110677
0.8116 Intermediate Similarity NPC163019
0.8116 Intermediate Similarity NPC1744
0.8102 Intermediate Similarity NPC159866
0.8102 Intermediate Similarity NPC64130
0.8102 Intermediate Similarity NPC175520
0.8102 Intermediate Similarity NPC295879
0.8102 Intermediate Similarity NPC25134
0.8102 Intermediate Similarity NPC97157
0.8088 Intermediate Similarity NPC205850
0.8074 Intermediate Similarity NPC214289
0.806 Intermediate Similarity NPC151617
0.806 Intermediate Similarity NPC76915
0.8029 Intermediate Similarity NPC173511
0.8029 Intermediate Similarity NPC137922
0.8029 Intermediate Similarity NPC474375
0.8029 Intermediate Similarity NPC40302
0.8029 Intermediate Similarity NPC88733
0.8 Intermediate Similarity NPC191194
0.7914 Intermediate Similarity NPC131940
0.7914 Intermediate Similarity NPC81149
0.7914 Intermediate Similarity NPC230013
0.7914 Intermediate Similarity NPC68350
0.7914 Intermediate Similarity NPC197576
0.7778 Intermediate Similarity NPC162294
0.7704 Intermediate Similarity NPC221301
0.7591 Intermediate Similarity NPC264379
0.7482 Intermediate Similarity NPC71186
0.7452 Intermediate Similarity NPC152947
0.7315 Intermediate Similarity NPC131128
0.7315 Intermediate Similarity NPC474134
0.7303 Intermediate Similarity NPC48956
0.7219 Intermediate Similarity NPC66840
0.7219 Intermediate Similarity NPC256307
0.7208 Intermediate Similarity NPC262189
0.719 Intermediate Similarity NPC474390
0.7185 Intermediate Similarity NPC124712
0.7182 Intermediate Similarity NPC156055
0.7152 Intermediate Similarity NPC95652
0.7152 Intermediate Similarity NPC150714
0.7143 Intermediate Similarity NPC319933
0.7111 Intermediate Similarity NPC232654
0.7097 Intermediate Similarity NPC20520
0.7097 Intermediate Similarity NPC22317
0.7097 Intermediate Similarity NPC61783
0.7095 Intermediate Similarity NPC37074
0.7063 Intermediate Similarity NPC281549
0.7047 Intermediate Similarity NPC247146
0.7039 Intermediate Similarity NPC60982
0.7037 Intermediate Similarity NPC307875
0.7032 Intermediate Similarity NPC55947
0.7027 Intermediate Similarity NPC469622
0.7027 Intermediate Similarity NPC298845
0.7027 Intermediate Similarity NPC189589
0.7025 Intermediate Similarity NPC171932
0.7025 Intermediate Similarity NPC28440
0.702 Intermediate Similarity NPC287780
0.7019 Intermediate Similarity NPC476969
0.7007 Intermediate Similarity NPC221090
0.698 Remote Similarity NPC216836
0.6974 Remote Similarity NPC161203
0.6954 Remote Similarity NPC60756
0.6954 Remote Similarity NPC214860
0.6954 Remote Similarity NPC208769
0.6939 Remote Similarity NPC192810
0.6928 Remote Similarity NPC37196
0.6928 Remote Similarity NPC94236
0.6918 Remote Similarity NPC145780
0.6892 Remote Similarity NPC228972
0.6892 Remote Similarity NPC25817
0.6892 Remote Similarity NPC122792
0.6887 Remote Similarity NPC45824
0.6887 Remote Similarity NPC210655
0.6883 Remote Similarity NPC245386
0.6883 Remote Similarity NPC310854
0.6883 Remote Similarity NPC106215
0.6871 Remote Similarity NPC152722
0.6867 Remote Similarity NPC50368
0.6867 Remote Similarity NPC470699
0.6867 Remote Similarity NPC210355
0.6867 Remote Similarity NPC469621
0.6863 Remote Similarity NPC86655
0.6863 Remote Similarity NPC202762
0.6859 Remote Similarity NPC102904
0.6859 Remote Similarity NPC271942
0.6859 Remote Similarity NPC103976
0.6859 Remote Similarity NPC326797
0.6859 Remote Similarity NPC176051
0.6859 Remote Similarity NPC107551
0.6859 Remote Similarity NPC474282
0.6859 Remote Similarity NPC276490
0.6842 Remote Similarity NPC91291
0.6842 Remote Similarity NPC229231
0.6839 Remote Similarity NPC472337
0.6839 Remote Similarity NPC281521
0.6839 Remote Similarity NPC255147
0.6839 Remote Similarity NPC283009
0.6839 Remote Similarity NPC201357
0.6839 Remote Similarity NPC134968
0.6839 Remote Similarity NPC261873
0.6835 Remote Similarity NPC118794
0.6824 Remote Similarity NPC217854
0.6821 Remote Similarity NPC266691
0.6821 Remote Similarity NPC46274
0.6821 Remote Similarity NPC226331
0.6821 Remote Similarity NPC469979
0.6818 Remote Similarity NPC229442
0.6818 Remote Similarity NPC168059
0.6815 Remote Similarity NPC127218
0.6815 Remote Similarity NPC319647
0.6815 Remote Similarity NPC25966
0.6815 Remote Similarity NPC245207
0.6815 Remote Similarity NPC22517
0.681 Remote Similarity NPC7398
0.681 Remote Similarity NPC211561
0.68 Remote Similarity NPC181361
0.6798 Remote Similarity NPC471591
0.6797 Remote Similarity NPC472597
0.6795 Remote Similarity NPC472334
0.6795 Remote Similarity NPC472336
0.679 Remote Similarity NPC170103
0.679 Remote Similarity NPC262911
0.679 Remote Similarity NPC204770
0.679 Remote Similarity NPC18185
0.679 Remote Similarity NPC82917
0.679 Remote Similarity NPC58190
0.679 Remote Similarity NPC294558
0.679 Remote Similarity NPC108811
0.679 Remote Similarity NPC202742
0.679 Remote Similarity NPC263940
0.679 Remote Similarity NPC70409
0.679 Remote Similarity NPC236202
0.6786 Remote Similarity NPC36077
0.6782 Remote Similarity NPC473462
0.6782 Remote Similarity NPC110454
0.6782 Remote Similarity NPC126128
0.6782 Remote Similarity NPC207819
0.6782 Remote Similarity NPC298981
0.6776 Remote Similarity NPC58164
0.6776 Remote Similarity NPC10225
0.6774 Remote Similarity NPC103967
0.6774 Remote Similarity NPC170694
0.6772 Remote Similarity NPC266197
0.6772 Remote Similarity NPC291101
0.6768 Remote Similarity NPC477612
0.676 Remote Similarity NPC82741
0.676 Remote Similarity NPC141405
0.676 Remote Similarity NPC473409
0.6757 Remote Similarity NPC473411
0.6757 Remote Similarity NPC71579
0.6757 Remote Similarity NPC262253
0.6755 Remote Similarity NPC5447
0.6755 Remote Similarity NPC250432
0.6753 Remote Similarity NPC160991
0.6753 Remote Similarity NPC16208
0.6753 Remote Similarity NPC184447
0.6753 Remote Similarity NPC127624
0.6753 Remote Similarity NPC35932
0.6753 Remote Similarity NPC470752
0.6753 Remote Similarity NPC7903
0.6752 Remote Similarity NPC73535
0.6752 Remote Similarity NPC25111
0.6752 Remote Similarity NPC272157
0.6752 Remote Similarity NPC211549
0.6752 Remote Similarity NPC90615
0.6752 Remote Similarity NPC6262
0.6752 Remote Similarity NPC201145
0.675 Remote Similarity NPC173203
0.675 Remote Similarity NPC163508
0.6748 Remote Similarity NPC20757
0.6748 Remote Similarity NPC329836
0.6748 Remote Similarity NPC227516
0.6746 Remote Similarity NPC36354
0.6735 Remote Similarity NPC276195
0.6732 Remote Similarity NPC51840
0.6732 Remote Similarity NPC299221
0.6732 Remote Similarity NPC234488
0.6732 Remote Similarity NPC220935
0.6732 Remote Similarity NPC472338
0.6732 Remote Similarity NPC311680

  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 NPC8577 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
0.6821 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6755 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6645 Remote Similarity NPD1613 Approved
0.6645 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6558 Remote Similarity NPD3027 Phase 3
0.6449 Remote Similarity NPD291 Approved
0.6387 Remote Similarity NPD4908 Phase 1
0.6374 Remote Similarity NPD4288 Approved
0.637 Remote Similarity NPD9296 Approved
0.6309 Remote Similarity NPD1548 Phase 1
0.6306 Remote Similarity NPD4907 Clinical (unspecified phase)
0.627 Remote Similarity NPD4287 Approved
0.6221 Remote Similarity NPD2801 Approved
0.6178 Remote Similarity NPD3537 Clinical (unspecified phase)
0.6178 Remote Similarity NPD8095 Phase 1
0.6165 Remote Similarity NPD9094 Approved
0.6154 Remote Similarity NPD968 Approved
0.6144 Remote Similarity NPD1610 Phase 2
0.6135 Remote Similarity NPD3454 Phase 3
0.6133 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6118 Remote Similarity NPD1653 Approved
0.6093 Remote Similarity NPD7533 Approved
0.6093 Remote Similarity NPD7534 Approved
0.6089 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6089 Remote Similarity NPD6166 Phase 2
0.6089 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6071 Remote Similarity NPD1511 Approved
0.6069 Remote Similarity NPD1934 Approved
0.6065 Remote Similarity NPD2982 Phase 2
0.6065 Remote Similarity NPD2983 Phase 2
0.6057 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6029 Remote Similarity NPD9365 Approved
0.6027 Remote Similarity NPD556 Approved
0.6 Remote Similarity NPD2981 Phase 2
0.6 Remote Similarity NPD1512 Approved
0.6 Remote Similarity NPD9295 Approved
0.5974 Remote Similarity NPD915 Approved
0.5938 Remote Similarity NPD4625 Phase 3
0.5935 Remote Similarity NPD1091 Approved
0.5926 Remote Similarity NPD1558 Phase 1
0.5924 Remote Similarity NPD7993 Clinical (unspecified phase)
0.5912 Remote Similarity NPD3018 Phase 2
0.5886 Remote Similarity NPD3827 Clinical (unspecified phase)
0.5882 Remote Similarity NPD8053 Approved
0.5882 Remote Similarity NPD7213 Phase 3
0.5882 Remote Similarity NPD7212 Phase 2
0.5882 Remote Similarity NPD8054 Approved
0.5864 Remote Similarity NPD6233 Phase 2
0.586 Remote Similarity NPD4379 Clinical (unspecified phase)
0.586 Remote Similarity NPD4749 Approved
0.5852 Remote Similarity NPD2393 Clinical (unspecified phase)
0.5848 Remote Similarity NPD7447 Phase 1
0.5839 Remote Similarity NPD228 Approved
0.5833 Remote Similarity NPD422 Phase 1
0.5823 Remote Similarity NPD3225 Approved
0.5815 Remote Similarity NPD5844 Phase 1
0.5815 Remote Similarity NPD7054 Approved
0.5813 Remote Similarity NPD2861 Phase 2
0.5801 Remote Similarity NPD4010 Discontinued
0.5787 Remote Similarity NPD3882 Suspended
0.5784 Remote Similarity NPD7074 Phase 3
0.5784 Remote Similarity NPD7472 Approved
0.5775 Remote Similarity NPD4338 Clinical (unspecified phase)
0.5775 Remote Similarity NPD7549 Discontinued
0.5771 Remote Similarity NPD4678 Approved
0.5771 Remote Similarity NPD4675 Approved
0.5763 Remote Similarity NPD1465 Phase 2
0.5724 Remote Similarity NPD9299 Approved
0.5723 Remote Similarity NPD2183 Approved
0.5723 Remote Similarity NPD2184 Approved
0.5722 Remote Similarity NPD6234 Discontinued
0.5714 Remote Similarity NPD9089 Approved
0.5706 Remote Similarity NPD6859 Clinical (unspecified phase)
0.5706 Remote Similarity NPD3750 Approved
0.5705 Remote Similarity NPD6516 Phase 2
0.5705 Remote Similarity NPD5846 Approved
0.5686 Remote Similarity NPD6671 Approved
0.5676 Remote Similarity NPD9552 Approved
0.5676 Remote Similarity NPD7228 Approved
0.5676 Remote Similarity NPD290 Approved
0.5676 Remote Similarity NPD3818 Discontinued
0.5668 Remote Similarity NPD6797 Phase 2
0.5665 Remote Similarity NPD7410 Clinical (unspecified phase)
0.5659 Remote Similarity NPD7199 Phase 2
0.5642 Remote Similarity NPD3817 Phase 2
0.5642 Remote Similarity NPD2296 Approved
0.5642 Remote Similarity NPD5402 Approved
0.5639 Remote Similarity NPD9093 Approved
0.5638 Remote Similarity NPD7251 Discontinued
0.5633 Remote Similarity NPD1535 Discovery
0.5632 Remote Similarity NPD1940 Clinical (unspecified phase)
0.5628 Remote Similarity NPD3787 Discontinued
0.5621 Remote Similarity NPD1552 Clinical (unspecified phase)
0.5621 Remote Similarity NPD1550 Clinical (unspecified phase)
0.5611 Remote Similarity NPD7768 Phase 2
0.561 Remote Similarity NPD6410 Clinical (unspecified phase)
0.5608 Remote Similarity NPD7808 Phase 3
0.5607 Remote Similarity NPD4357 Discontinued
0.56 Remote Similarity NPD5403 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