Structure

Physi-Chem Properties

Molecular Weight:  402.24
Volume:  446.52
LogP:  4.494
LogD:  4.196
LogS:  -4.388
# Rotatable Bonds:  15
TPSA:  80.67
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.18
Synthetic Accessibility Score:  3.249
Fsp3:  0.458
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:  -5.084
MDCK Permeability:  1.4038963854545727e-05
Pgp-inhibitor:  0.013
Pgp-substrate:  0.578
Human Intestinal Absorption (HIA):  0.8
20% Bioavailability (F20%):  0.396
30% Bioavailability (F30%):  0.303

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.011
Plasma Protein Binding (PPB):  89.45845794677734%
Volume Distribution (VD):  0.531
Pgp-substrate:  2.09588623046875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.333
CYP1A2-substrate:  0.118
CYP2C19-inhibitor:  0.106
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.812
CYP2C9-substrate:  0.996
CYP2D6-inhibitor:  0.808
CYP2D6-substrate:  0.77
CYP3A4-inhibitor:  0.12
CYP3A4-substrate:  0.073

ADMET: Excretion

Clearance (CL):  2.167
Half-life (T1/2):  0.871

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.382
Drug-inuced Liver Injury (DILI):  0.005
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.741
Skin Sensitization:  0.985
Carcinogencity:  0.017
Eye Corrosion:  0.964
Eye Irritation:  0.911
Respiratory Toxicity:  0.869

Download Data

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

  Natural Product: NPC82465

Natural Product ID:  NPC82465
Common Name*:   Boletinin G
IUPAC Name:   (E)-4-oxo-4-[(2E,6E,10E,14E)-3,7,11,15-tetramethyl-16-oxohexadeca-2,6,10,14-tetraenoxy]but-2-enoic acid
Synonyms:   Boletinin G
Standard InCHIKey:  IPFUHLGHDLEPJG-KCSPCAOWSA-N
Standard InCHI:  InChI=1S/C24H34O5/c1-19(8-5-9-20(2)11-7-13-22(4)18-25)10-6-12-21(3)16-17-29-24(28)15-14-23(26)27/h9-10,13-16,18H,5-8,11-12,17H2,1-4H3,(H,26,27)/b15-14+,19-10+,20-9+,21-16+,22-13+
SMILES:  C/C(=CCC/C(=C/COC(=O)/C=C/C(=O)O)/C)/CC/C=C(C)/CC/C=C(C)/C=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL470261
PubChem CID:   11750010
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0001357] Acyclic 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
NPO28298 Boletinus cavipes Species Gyrodontaceae Eukaryota n.a. n.a. n.a. PMID[15217273]
NPO28298 Boletinus cavipes Species Gyrodontaceae 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
NPT2 Others Unspecified Inhibition = 26.0 % PMID[507673]
NPT27 Others Unspecified Activity = 58.0 % PMID[507673]
NPT27 Others Unspecified Activity = 22.0 % PMID[507673]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Inhibition = 0.0 % PMID[507673]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Inhibition = 6.0 % PMID[507673]

☑ 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 NPC82465 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
0.9818 High Similarity NPC21946
0.9464 High Similarity NPC254095
0.9286 High Similarity NPC294938
0.9286 High Similarity NPC293437
0.9286 High Similarity NPC249850
0.9286 High Similarity NPC129150
0.9123 High Similarity NPC223679
0.8947 High Similarity NPC135863
0.8364 Intermediate Similarity NPC236338
0.8226 Intermediate Similarity NPC68110
0.8036 Intermediate Similarity NPC15789
0.7903 Intermediate Similarity NPC79756
0.7818 Intermediate Similarity NPC128280
0.7818 Intermediate Similarity NPC197467
0.7818 Intermediate Similarity NPC308331
0.7778 Intermediate Similarity NPC26810
0.7692 Intermediate Similarity NPC282760
0.7692 Intermediate Similarity NPC273600
0.7656 Intermediate Similarity NPC473737
0.7636 Intermediate Similarity NPC47946
0.7636 Intermediate Similarity NPC26600
0.7636 Intermediate Similarity NPC270706
0.7586 Intermediate Similarity NPC43053
0.7576 Intermediate Similarity NPC146811
0.7544 Intermediate Similarity NPC135698
0.7536 Intermediate Similarity NPC316185
0.75 Intermediate Similarity NPC55376
0.75 Intermediate Similarity NPC478120
0.75 Intermediate Similarity NPC151481
0.746 Intermediate Similarity NPC97570
0.7455 Intermediate Similarity NPC6963
0.7455 Intermediate Similarity NPC304079
0.7419 Intermediate Similarity NPC283502
0.7391 Intermediate Similarity NPC59558
0.7385 Intermediate Similarity NPC44343
0.7385 Intermediate Similarity NPC179087
0.7385 Intermediate Similarity NPC210303
0.7361 Intermediate Similarity NPC203277
0.7344 Intermediate Similarity NPC130953
0.7344 Intermediate Similarity NPC98519
0.7324 Intermediate Similarity NPC315843
0.7313 Intermediate Similarity NPC475675
0.7313 Intermediate Similarity NPC475555
0.7302 Intermediate Similarity NPC189700
0.7302 Intermediate Similarity NPC474084
0.7286 Intermediate Similarity NPC293114
0.7231 Intermediate Similarity NPC151648
0.7213 Intermediate Similarity NPC474127
0.7206 Intermediate Similarity NPC203335
0.7206 Intermediate Similarity NPC122627
0.7183 Intermediate Similarity NPC284006
0.7164 Intermediate Similarity NPC19769
0.7164 Intermediate Similarity NPC471565
0.7164 Intermediate Similarity NPC471566
0.7164 Intermediate Similarity NPC96414
0.7162 Intermediate Similarity NPC279532
0.7143 Intermediate Similarity NPC476037
0.7143 Intermediate Similarity NPC12907
0.7143 Intermediate Similarity NPC265551
0.7143 Intermediate Similarity NPC212730
0.7121 Intermediate Similarity NPC2328
0.7097 Intermediate Similarity NPC478117
0.7091 Intermediate Similarity NPC57923
0.7091 Intermediate Similarity NPC41409
0.7083 Intermediate Similarity NPC107654
0.7077 Intermediate Similarity NPC471278
0.7077 Intermediate Similarity NPC26223
0.7059 Intermediate Similarity NPC201356
0.7059 Intermediate Similarity NPC248125
0.7051 Intermediate Similarity NPC161670
0.7049 Intermediate Similarity NPC477780
0.7049 Intermediate Similarity NPC477781
0.7015 Intermediate Similarity NPC470808
0.7 Intermediate Similarity NPC475982
0.6986 Remote Similarity NPC260396
0.6984 Remote Similarity NPC221763
0.6984 Remote Similarity NPC245002
0.6984 Remote Similarity NPC96663
0.6984 Remote Similarity NPC150717
0.6984 Remote Similarity NPC51846
0.6957 Remote Similarity NPC478097
0.6957 Remote Similarity NPC225272
0.6944 Remote Similarity NPC329890
0.6944 Remote Similarity NPC474705
0.6935 Remote Similarity NPC218486
0.6935 Remote Similarity NPC159535
0.6935 Remote Similarity NPC151761
0.6933 Remote Similarity NPC473471
0.6923 Remote Similarity NPC302564
0.6923 Remote Similarity NPC286189
0.6912 Remote Similarity NPC478099
0.6912 Remote Similarity NPC471556
0.6912 Remote Similarity NPC470123
0.6912 Remote Similarity NPC478098
0.6909 Remote Similarity NPC221250
0.6901 Remote Similarity NPC476012
0.6901 Remote Similarity NPC202011
0.6901 Remote Similarity NPC469660
0.6892 Remote Similarity NPC205615
0.6892 Remote Similarity NPC256640
0.6892 Remote Similarity NPC16279
0.6885 Remote Similarity NPC106531
0.6875 Remote Similarity NPC268185
0.6875 Remote Similarity NPC471279
0.6875 Remote Similarity NPC471277
0.6875 Remote Similarity NPC211892
0.6866 Remote Similarity NPC155849
0.6857 Remote Similarity NPC218477
0.6857 Remote Similarity NPC477117
0.6857 Remote Similarity NPC474823
0.6849 Remote Similarity NPC470686
0.6849 Remote Similarity NPC114727
0.6849 Remote Similarity NPC476590
0.6835 Remote Similarity NPC474865
0.6833 Remote Similarity NPC221467
0.6833 Remote Similarity NPC275316
0.6833 Remote Similarity NPC27264
0.6825 Remote Similarity NPC474913
0.6818 Remote Similarity NPC309408
0.6812 Remote Similarity NPC478101
0.6806 Remote Similarity NPC84038
0.68 Remote Similarity NPC49302
0.68 Remote Similarity NPC474818
0.68 Remote Similarity NPC125365
0.68 Remote Similarity NPC176329
0.68 Remote Similarity NPC275530
0.68 Remote Similarity NPC51809
0.6769 Remote Similarity NPC471619
0.6765 Remote Similarity NPC34883
0.6765 Remote Similarity NPC148233
0.6765 Remote Similarity NPC25747
0.6765 Remote Similarity NPC308457
0.6761 Remote Similarity NPC88877
0.6761 Remote Similarity NPC476591
0.6761 Remote Similarity NPC475004
0.6757 Remote Similarity NPC478195
0.6757 Remote Similarity NPC478192
0.6757 Remote Similarity NPC478193
0.6757 Remote Similarity NPC478194
0.6757 Remote Similarity NPC478191
0.6757 Remote Similarity NPC478196
0.6727 Remote Similarity NPC8270
0.6727 Remote Similarity NPC12319
0.6727 Remote Similarity NPC18205
0.6727 Remote Similarity NPC281043
0.6724 Remote Similarity NPC160628
0.6721 Remote Similarity NPC148056
0.6719 Remote Similarity NPC472808
0.6719 Remote Similarity NPC324224
0.6716 Remote Similarity NPC263732
0.6714 Remote Similarity NPC132286
0.6714 Remote Similarity NPC478100
0.6714 Remote Similarity NPC194871
0.6712 Remote Similarity NPC185186
0.6712 Remote Similarity NPC316851
0.6712 Remote Similarity NPC287878
0.6712 Remote Similarity NPC327383
0.6712 Remote Similarity NPC329914
0.6711 Remote Similarity NPC221095
0.6711 Remote Similarity NPC108816
0.6711 Remote Similarity NPC93763
0.6711 Remote Similarity NPC279214
0.6709 Remote Similarity NPC161045
0.6667 Remote Similarity NPC127118
0.6667 Remote Similarity NPC67183
0.6667 Remote Similarity NPC15912
0.6667 Remote Similarity NPC473361
0.6667 Remote Similarity NPC222852
0.6667 Remote Similarity NPC116934
0.6667 Remote Similarity NPC269615
0.6667 Remote Similarity NPC301207
0.6667 Remote Similarity NPC133904
0.6667 Remote Similarity NPC159650
0.6667 Remote Similarity NPC470688
0.6667 Remote Similarity NPC267110
0.6667 Remote Similarity NPC182794
0.6667 Remote Similarity NPC188860
0.6667 Remote Similarity NPC209113
0.6667 Remote Similarity NPC4299
0.6667 Remote Similarity NPC329904
0.6667 Remote Similarity NPC112868
0.6667 Remote Similarity NPC22897
0.6667 Remote Similarity NPC7940
0.6667 Remote Similarity NPC322186
0.6627 Remote Similarity NPC83423
0.6622 Remote Similarity NPC474758
0.662 Remote Similarity NPC238223
0.662 Remote Similarity NPC287705
0.662 Remote Similarity NPC63873
0.662 Remote Similarity NPC470256
0.6618 Remote Similarity NPC475073
0.6618 Remote Similarity NPC217940
0.6618 Remote Similarity NPC474658
0.6618 Remote Similarity NPC474774
0.6615 Remote Similarity NPC44542
0.6615 Remote Similarity NPC472445
0.6615 Remote Similarity NPC71755
0.6613 Remote Similarity NPC191643
0.6613 Remote Similarity NPC151919
0.661 Remote Similarity NPC87137

  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 NPC82465 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
0.7895 Intermediate Similarity NPD6927 Phase 3
0.7544 Intermediate Similarity NPD4220 Pre-registration
0.6842 Remote Similarity NPD6096 Approved
0.6842 Remote Similarity NPD6097 Approved
0.678 Remote Similarity NPD5343 Approved
0.6522 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6441 Remote Similarity NPD4265 Approved
0.6441 Remote Similarity NPD39 Approved
0.6429 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6379 Remote Similarity NPD5326 Phase 3
0.6379 Remote Similarity NPD9411 Phase 1
0.6324 Remote Similarity NPD4246 Clinical (unspecified phase)
0.629 Remote Similarity NPD2268 Discontinued
0.6269 Remote Similarity NPD6109 Phase 1
0.6232 Remote Similarity NPD4193 Approved
0.6232 Remote Similarity NPD4194 Approved
0.6232 Remote Similarity NPD4192 Approved
0.6232 Remote Similarity NPD4191 Approved
0.6182 Remote Similarity NPD9115 Approved
0.6167 Remote Similarity NPD4222 Approved
0.6027 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6024 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5977 Remote Similarity NPD7838 Discovery
0.5976 Remote Similarity NPD5209 Approved
0.5949 Remote Similarity NPD4756 Discovery
0.5897 Remote Similarity NPD1452 Discontinued
0.5897 Remote Similarity NPD8039 Approved
0.5873 Remote Similarity NPD3173 Approved
0.5797 Remote Similarity NPD585 Clinical (unspecified phase)
0.5795 Remote Similarity NPD5785 Approved
0.5783 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5775 Remote Similarity NPD9418 Clinical (unspecified phase)
0.5732 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7154 Phase 3
0.5699 Remote Similarity NPD8029 Clinical (unspecified phase)
0.569 Remote Similarity NPD5783 Phase 3
0.5672 Remote Similarity NPD3194 Approved
0.5672 Remote Similarity NPD3196 Approved
0.5672 Remote Similarity NPD4266 Approved
0.5672 Remote Similarity NPD3195 Phase 2
0.5652 Remote Similarity NPD8779 Phase 3
0.5645 Remote Similarity NPD3174 Discontinued
0.5636 Remote Similarity NPD8573 Approved
0.5618 Remote Similarity NPD6698 Approved
0.5618 Remote Similarity NPD46 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