Structure

Physi-Chem Properties

Molecular Weight:  432.25
Volume:  472.606
LogP:  5.17
LogD:  4.779
LogS:  -3.902
# Rotatable Bonds:  15
TPSA:  100.9
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.21
Synthetic Accessibility Score:  3.862
Fsp3:  0.48
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.48
MDCK Permeability:  6.193421722855419e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.023
Human Intestinal Absorption (HIA):  0.964
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  96.06839752197266%
Volume Distribution (VD):  0.342
Pgp-substrate:  1.4722412824630737%

ADMET: Metabolism

CYP1A2-inhibitor:  0.097
CYP1A2-substrate:  0.098
CYP2C19-inhibitor:  0.057
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.806
CYP2C9-substrate:  0.97
CYP2D6-inhibitor:  0.644
CYP2D6-substrate:  0.1
CYP3A4-inhibitor:  0.046
CYP3A4-substrate:  0.033

ADMET: Excretion

Clearance (CL):  1.46
Half-life (T1/2):  0.837

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.789
Drug-inuced Liver Injury (DILI):  0.014
AMES Toxicity:  0.0
Rat Oral Acute Toxicity:  0.001
Maximum Recommended Daily Dose:  0.111
Skin Sensitization:  0.974
Carcinogencity:  0.005
Eye Corrosion:  0.181
Eye Irritation:  0.603
Respiratory Toxicity:  0.169

Download Data

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

  Natural Product: NPC293437

Natural Product ID:  NPC293437
Common Name*:   Boletinin J
IUPAC Name:   (2E,6E,10E,14E)-16-[(E)-3-carboxy-2-methylprop-2-enoyl]oxy-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraenoic acid
Synonyms:   Boletinin J
Standard InCHIKey:  RGDGFPUBWJTQHJ-HGJUBKMSSA-N
Standard InCHI:  InChI=1S/C25H36O6/c1-18(9-6-10-19(2)13-8-14-21(4)24(28)29)11-7-12-20(3)15-16-31-25(30)22(5)17-23(26)27/h10-11,14-15,17H,6-9,12-13,16H2,1-5H3,(H,26,27)(H,28,29)/b18-11+,19-10+,20-15+,21-14+,22-17+
SMILES:  C/C(=CCC/C(=C/COC(=O)/C(=C/C(=O)O)/C)/C)/CC/C=C(C)/CC/C=C(C)/C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL471069
PubChem CID:   11362497
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 = 21.0 % PMID[534426]
NPT27 Others Unspecified Activity = 47.0 % PMID[534426]
NPT27 Others Unspecified Activity = 27.0 % PMID[534426]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Inhibition = -5.0 % PMID[534426]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Inhibition = 20.0 % PMID[534426]

☑ 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 NPC293437 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 NPC249850
0.9815 High Similarity NPC254095
0.963 High Similarity NPC135863
0.9455 High Similarity NPC223679
0.9455 High Similarity NPC21946
0.9286 High Similarity NPC82465
0.9273 High Similarity NPC129150
0.9273 High Similarity NPC294938
0.8814 High Similarity NPC68110
0.8679 High Similarity NPC236338
0.8226 Intermediate Similarity NPC282760
0.8167 Intermediate Similarity NPC79756
0.8113 Intermediate Similarity NPC308331
0.8113 Intermediate Similarity NPC197467
0.8113 Intermediate Similarity NPC128280
0.8033 Intermediate Similarity NPC26810
0.8 Intermediate Similarity NPC15789
0.7966 Intermediate Similarity NPC283502
0.7937 Intermediate Similarity NPC273600
0.7925 Intermediate Similarity NPC26600
0.7925 Intermediate Similarity NPC47946
0.7925 Intermediate Similarity NPC270706
0.7857 Intermediate Similarity NPC43053
0.7818 Intermediate Similarity NPC135698
0.7812 Intermediate Similarity NPC146811
0.7761 Intermediate Similarity NPC316185
0.7742 Intermediate Similarity NPC55376
0.7736 Intermediate Similarity NPC6963
0.7736 Intermediate Similarity NPC304079
0.7705 Intermediate Similarity NPC97570
0.7619 Intermediate Similarity NPC473737
0.7612 Intermediate Similarity NPC59558
0.7571 Intermediate Similarity NPC203277
0.7541 Intermediate Similarity NPC474084
0.7538 Intermediate Similarity NPC475675
0.7538 Intermediate Similarity NPC475555
0.7536 Intermediate Similarity NPC315843
0.75 Intermediate Similarity NPC293114
0.7463 Intermediate Similarity NPC151481
0.746 Intermediate Similarity NPC151648
0.7458 Intermediate Similarity NPC478120
0.7458 Intermediate Similarity NPC474127
0.7424 Intermediate Similarity NPC203335
0.7424 Intermediate Similarity NPC122627
0.7391 Intermediate Similarity NPC284006
0.7385 Intermediate Similarity NPC470123
0.7385 Intermediate Similarity NPC96414
0.7385 Intermediate Similarity NPC19769
0.7385 Intermediate Similarity NPC471565
0.7385 Intermediate Similarity NPC471556
0.7385 Intermediate Similarity NPC471566
0.7377 Intermediate Similarity NPC268185
0.7361 Intermediate Similarity NPC279532
0.7353 Intermediate Similarity NPC476037
0.7353 Intermediate Similarity NPC202011
0.7344 Intermediate Similarity NPC210303
0.7344 Intermediate Similarity NPC44343
0.7344 Intermediate Similarity NPC2328
0.7344 Intermediate Similarity NPC179087
0.7324 Intermediate Similarity NPC16279
0.7324 Intermediate Similarity NPC205615
0.7324 Intermediate Similarity NPC256640
0.7302 Intermediate Similarity NPC98519
0.7302 Intermediate Similarity NPC130953
0.7286 Intermediate Similarity NPC476590
0.7286 Intermediate Similarity NPC114727
0.7286 Intermediate Similarity NPC107654
0.7273 Intermediate Similarity NPC201356
0.7273 Intermediate Similarity NPC160628
0.7273 Intermediate Similarity NPC248125
0.7258 Intermediate Similarity NPC471619
0.7258 Intermediate Similarity NPC189700
0.7222 Intermediate Similarity NPC49302
0.7222 Intermediate Similarity NPC125365
0.7222 Intermediate Similarity NPC474818
0.7222 Intermediate Similarity NPC51809
0.7222 Intermediate Similarity NPC116934
0.7222 Intermediate Similarity NPC176329
0.7213 Intermediate Similarity NPC96663
0.7213 Intermediate Similarity NPC51846
0.7206 Intermediate Similarity NPC475982
0.7193 Intermediate Similarity NPC267110
0.7183 Intermediate Similarity NPC478194
0.7183 Intermediate Similarity NPC478191
0.7183 Intermediate Similarity NPC478196
0.7183 Intermediate Similarity NPC478193
0.7183 Intermediate Similarity NPC478195
0.7183 Intermediate Similarity NPC478192
0.7183 Intermediate Similarity NPC260396
0.7167 Intermediate Similarity NPC218486
0.7164 Intermediate Similarity NPC132286
0.7164 Intermediate Similarity NPC478097
0.7143 Intermediate Similarity NPC286189
0.7143 Intermediate Similarity NPC302564
0.7143 Intermediate Similarity NPC87137
0.7143 Intermediate Similarity NPC329890
0.7123 Intermediate Similarity NPC279214
0.7123 Intermediate Similarity NPC221095
0.7123 Intermediate Similarity NPC93763
0.7123 Intermediate Similarity NPC473471
0.7123 Intermediate Similarity NPC108816
0.7121 Intermediate Similarity NPC478099
0.7121 Intermediate Similarity NPC478098
0.7101 Intermediate Similarity NPC67183
0.7101 Intermediate Similarity NPC476012
0.7101 Intermediate Similarity NPC329904
0.7101 Intermediate Similarity NPC4299
0.7101 Intermediate Similarity NPC469660
0.7101 Intermediate Similarity NPC473361
0.7097 Intermediate Similarity NPC212730
0.7097 Intermediate Similarity NPC265551
0.7091 Intermediate Similarity NPC12907
0.7083 Intermediate Similarity NPC301207
0.7077 Intermediate Similarity NPC475073
0.7077 Intermediate Similarity NPC155849
0.7069 Intermediate Similarity NPC221467
0.7059 Intermediate Similarity NPC474823
0.7059 Intermediate Similarity NPC238223
0.7059 Intermediate Similarity NPC287705
0.7049 Intermediate Similarity NPC478117
0.7049 Intermediate Similarity NPC49028
0.7037 Intermediate Similarity NPC41409
0.7037 Intermediate Similarity NPC57923
0.7031 Intermediate Similarity NPC26223
0.7031 Intermediate Similarity NPC471278
0.7015 Intermediate Similarity NPC478101
0.7 Intermediate Similarity NPC477087
0.7 Intermediate Similarity NPC477781
0.7 Intermediate Similarity NPC477780
0.7 Intermediate Similarity NPC84038
0.7 Intermediate Similarity NPC477086
0.697 Remote Similarity NPC470808
0.6964 Remote Similarity NPC140501
0.6957 Remote Similarity NPC476591
0.6957 Remote Similarity NPC101622
0.6957 Remote Similarity NPC88877
0.6957 Remote Similarity NPC475004
0.6944 Remote Similarity NPC329852
0.6935 Remote Similarity NPC324224
0.6935 Remote Similarity NPC221763
0.6935 Remote Similarity NPC150717
0.6935 Remote Similarity NPC245002
0.6935 Remote Similarity NPC472808
0.6923 Remote Similarity NPC263732
0.6912 Remote Similarity NPC225272
0.6912 Remote Similarity NPC478100
0.6912 Remote Similarity NPC194871
0.6901 Remote Similarity NPC185186
0.6901 Remote Similarity NPC327383
0.6901 Remote Similarity NPC329914
0.6901 Remote Similarity NPC474705
0.6901 Remote Similarity NPC477085
0.6901 Remote Similarity NPC144419
0.6901 Remote Similarity NPC316851
0.6892 Remote Similarity NPC209135
0.6892 Remote Similarity NPC474816
0.6892 Remote Similarity NPC477314
0.6885 Remote Similarity NPC154626
0.6885 Remote Similarity NPC151761
0.6885 Remote Similarity NPC189677
0.6885 Remote Similarity NPC159535
0.6883 Remote Similarity NPC286770
0.6883 Remote Similarity NPC284472
0.6883 Remote Similarity NPC161045
0.6883 Remote Similarity NPC229799
0.6875 Remote Similarity NPC322186
0.6875 Remote Similarity NPC222852
0.6857 Remote Similarity NPC315597
0.6857 Remote Similarity NPC315285
0.6852 Remote Similarity NPC221250
0.6852 Remote Similarity NPC269823
0.6849 Remote Similarity NPC209113
0.6849 Remote Similarity NPC188860
0.6849 Remote Similarity NPC68819
0.6849 Remote Similarity NPC477202
0.6849 Remote Similarity NPC469880
0.6849 Remote Similarity NPC127118
0.6842 Remote Similarity NPC112868
0.6833 Remote Similarity NPC106531
0.6833 Remote Similarity NPC191643
0.6825 Remote Similarity NPC472445
0.6825 Remote Similarity NPC71755
0.6825 Remote Similarity NPC471277
0.6825 Remote Similarity NPC471279
0.6818 Remote Similarity NPC217940
0.6818 Remote Similarity NPC474658
0.6812 Remote Similarity NPC63873
0.6812 Remote Similarity NPC218477
0.6812 Remote Similarity NPC470256
0.6812 Remote Similarity NPC310210
0.6806 Remote Similarity NPC470686
0.6806 Remote Similarity NPC474758
0.6795 Remote Similarity NPC161670
0.6795 Remote Similarity NPC474865
0.678 Remote Similarity NPC27264
0.678 Remote Similarity NPC225974
0.678 Remote Similarity NPC275316
0.6774 Remote Similarity NPC173157
0.6774 Remote Similarity NPC474913
0.6769 Remote Similarity NPC309408

  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 NPC293437 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
0.8182 Intermediate Similarity NPD6927 Phase 3
0.75 Intermediate Similarity NPD4220 Pre-registration
0.6964 Remote Similarity NPD4265 Approved
0.6909 Remote Similarity NPD9411 Phase 1
0.6786 Remote Similarity NPD6096 Approved
0.6786 Remote Similarity NPD6097 Approved
0.6724 Remote Similarity NPD5343 Approved
0.6667 Remote Similarity NPD39 Approved
0.6618 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5326 Phase 3
0.6515 Remote Similarity NPD4246 Clinical (unspecified phase)
0.65 Remote Similarity NPD2268 Discontinued
0.6471 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6462 Remote Similarity NPD6109 Phase 1
0.6379 Remote Similarity NPD4222 Approved
0.6375 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4756 Discovery
0.6197 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6176 Remote Similarity NPD4193 Approved
0.6176 Remote Similarity NPD4192 Approved
0.6176 Remote Similarity NPD4191 Approved
0.6176 Remote Similarity NPD4194 Approved
0.6118 Remote Similarity NPD7838 Discovery
0.6111 Remote Similarity NPD9115 Approved
0.6066 Remote Similarity NPD3173 Approved
0.6053 Remote Similarity NPD1452 Discontinued
0.597 Remote Similarity NPD585 Clinical (unspecified phase)
0.5942 Remote Similarity NPD9418 Clinical (unspecified phase)
0.593 Remote Similarity NPD6698 Approved
0.593 Remote Similarity NPD46 Approved
0.593 Remote Similarity NPD5785 Approved
0.5926 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5926 Remote Similarity NPD5209 Approved
0.5904 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5893 Remote Similarity NPD5783 Phase 3
0.5875 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5854 Remote Similarity NPD7154 Phase 3
0.5846 Remote Similarity NPD3195 Phase 2
0.5846 Remote Similarity NPD3194 Approved
0.5846 Remote Similarity NPD3196 Approved
0.5846 Remote Similarity NPD4266 Approved
0.5844 Remote Similarity NPD8039 Approved
0.5824 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5821 Remote Similarity NPD8779 Phase 3
0.5735 Remote Similarity NPD9119 Approved
0.5735 Remote Similarity NPD69 Approved
0.5714 Remote Similarity NPD5363 Approved
0.5692 Remote Similarity NPD3172 Approved
0.5663 Remote Similarity NPD5362 Discontinued
0.5652 Remote Similarity NPD4225 Approved
0.5625 Remote Similarity NPD4271 Approved
0.5625 Remote Similarity NPD4268 Approved
0.5625 Remote Similarity NPD5784 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