Structure

Physi-Chem Properties

Molecular Weight:  256.15
Volume:  299.077
LogP:  2.162
LogD:  2.228
LogS:  -3.397
# Rotatable Bonds:  7
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.562
Synthetic Accessibility Score:  3.694
Fsp3:  0.353
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -3.93
MDCK Permeability:  3.90301865991205e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.051
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  99.74918365478516%
Volume Distribution (VD):  0.51
Pgp-substrate:  2.2150700092315674%

ADMET: Metabolism

CYP1A2-inhibitor:  0.836
CYP1A2-substrate:  0.206
CYP2C19-inhibitor:  0.96
CYP2C19-substrate:  0.517
CYP2C9-inhibitor:  0.918
CYP2C9-substrate:  0.975
CYP2D6-inhibitor:  0.908
CYP2D6-substrate:  0.896
CYP3A4-inhibitor:  0.933
CYP3A4-substrate:  0.208

ADMET: Excretion

Clearance (CL):  7.309
Half-life (T1/2):  0.892

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.989
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.847
Rat Oral Acute Toxicity:  0.419
Maximum Recommended Daily Dose:  0.441
Skin Sensitization:  0.944
Carcinogencity:  0.799
Eye Corrosion:  0.906
Eye Irritation:  0.988
Respiratory Toxicity:  0.796

Download Data

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

  Natural Product: NPC61177

Natural Product ID:  NPC61177
Common Name*:   Bupleuronol
IUPAC Name:   (7E,9E,15Z)-17-hydroxyheptadeca-7,9,15-trien-11,13-diyn-4-one
Synonyms:   Bupleuronol
Standard InCHIKey:  ORKCFSINEADMSV-VJWXCIGJSA-N
Standard InCHI:  InChI=1S/C17H20O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10-11,13,18H,2,12,14-16H2,1H3/b6-4+,10-8+,13-11-
SMILES:  CCCC(=O)CC/C=C/C=C/C#CC#C/C=CCO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077019
PubChem CID:   46881232
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols
          • [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO16425 Bupleurum longiradiatum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[19994846]
NPO16425 Bupleurum longiradiatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16425 Bupleurum longiradiatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16425 Bupleurum longiradiatum Species Apiaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 11000.0 nM PMID[491454]

☑ 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 NPC61177 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
0.8846 High Similarity NPC284224
0.8462 Intermediate Similarity NPC71053
0.8462 Intermediate Similarity NPC59408
0.84 Intermediate Similarity NPC180575
0.8214 Intermediate Similarity NPC44542
0.8214 Intermediate Similarity NPC193975
0.8077 Intermediate Similarity NPC267110
0.8077 Intermediate Similarity NPC248884
0.8077 Intermediate Similarity NPC31194
0.8077 Intermediate Similarity NPC85079
0.8077 Intermediate Similarity NPC153538
0.8039 Intermediate Similarity NPC124183
0.8039 Intermediate Similarity NPC35141
0.8 Intermediate Similarity NPC110732
0.8 Intermediate Similarity NPC300121
0.8 Intermediate Similarity NPC48058
0.7959 Intermediate Similarity NPC206906
0.7931 Intermediate Similarity NPC473652
0.7925 Intermediate Similarity NPC291437
0.7925 Intermediate Similarity NPC72699
0.7925 Intermediate Similarity NPC328784
0.7857 Intermediate Similarity NPC471239
0.7843 Intermediate Similarity NPC269074
0.7818 Intermediate Similarity NPC217188
0.7797 Intermediate Similarity NPC327112
0.7778 Intermediate Similarity NPC151782
0.7778 Intermediate Similarity NPC93639
0.7736 Intermediate Similarity NPC471276
0.7736 Intermediate Similarity NPC471275
0.7736 Intermediate Similarity NPC302310
0.7736 Intermediate Similarity NPC125122
0.7736 Intermediate Similarity NPC471280
0.7692 Intermediate Similarity NPC55063
0.7692 Intermediate Similarity NPC19834
0.7679 Intermediate Similarity NPC189677
0.7667 Intermediate Similarity NPC168407
0.7647 Intermediate Similarity NPC101616
0.7636 Intermediate Similarity NPC142092
0.7627 Intermediate Similarity NPC222852
0.76 Intermediate Similarity NPC304151
0.7593 Intermediate Similarity NPC474642
0.7593 Intermediate Similarity NPC249670
0.7593 Intermediate Similarity NPC471281
0.7593 Intermediate Similarity NPC477727
0.7593 Intermediate Similarity NPC473913
0.7593 Intermediate Similarity NPC199286
0.7586 Intermediate Similarity NPC472445
0.7586 Intermediate Similarity NPC265551
0.7586 Intermediate Similarity NPC212730
0.7544 Intermediate Similarity NPC152668
0.7544 Intermediate Similarity NPC474513
0.7544 Intermediate Similarity NPC470963
0.7544 Intermediate Similarity NPC146551
0.75 Intermediate Similarity NPC34577
0.75 Intermediate Similarity NPC276825
0.7455 Intermediate Similarity NPC256656
0.7455 Intermediate Similarity NPC197272
0.7455 Intermediate Similarity NPC477723
0.7455 Intermediate Similarity NPC89824
0.7455 Intermediate Similarity NPC471959
0.7455 Intermediate Similarity NPC475477
0.7455 Intermediate Similarity NPC294278
0.7455 Intermediate Similarity NPC55383
0.7455 Intermediate Similarity NPC76198
0.7455 Intermediate Similarity NPC170776
0.7455 Intermediate Similarity NPC329608
0.7455 Intermediate Similarity NPC224148
0.7455 Intermediate Similarity NPC9273
0.7455 Intermediate Similarity NPC165447
0.7419 Intermediate Similarity NPC470320
0.7414 Intermediate Similarity NPC470964
0.7414 Intermediate Similarity NPC311648
0.7368 Intermediate Similarity NPC256209
0.7368 Intermediate Similarity NPC49059
0.7347 Intermediate Similarity NPC15934
0.7333 Intermediate Similarity NPC318306
0.7333 Intermediate Similarity NPC322186
0.7333 Intermediate Similarity NPC322002
0.7321 Intermediate Similarity NPC106531
0.7321 Intermediate Similarity NPC473705
0.7308 Intermediate Similarity NPC138935
0.7302 Intermediate Similarity NPC245947
0.7302 Intermediate Similarity NPC136164
0.7302 Intermediate Similarity NPC255863
0.7288 Intermediate Similarity NPC48968
0.7288 Intermediate Similarity NPC594
0.7273 Intermediate Similarity NPC473487
0.7213 Intermediate Similarity NPC471278
0.7213 Intermediate Similarity NPC328311
0.717 Intermediate Similarity NPC474202
0.717 Intermediate Similarity NPC474362
0.7143 Intermediate Similarity NPC226592
0.7143 Intermediate Similarity NPC129263
0.7121 Intermediate Similarity NPC143396
0.7121 Intermediate Similarity NPC236208
0.7119 Intermediate Similarity NPC324224
0.7119 Intermediate Similarity NPC472808
0.7097 Intermediate Similarity NPC477829
0.7097 Intermediate Similarity NPC66460
0.7097 Intermediate Similarity NPC325929
0.7097 Intermediate Similarity NPC271282
0.7069 Intermediate Similarity NPC269615
0.7069 Intermediate Similarity NPC473532
0.7049 Intermediate Similarity NPC329249
0.7031 Intermediate Similarity NPC323045
0.7031 Intermediate Similarity NPC317881
0.7 Intermediate Similarity NPC268185
0.6984 Remote Similarity NPC29697
0.6981 Remote Similarity NPC108195
0.6964 Remote Similarity NPC225974
0.6964 Remote Similarity NPC288381
0.6964 Remote Similarity NPC20934
0.6949 Remote Similarity NPC473735
0.6949 Remote Similarity NPC473721
0.6949 Remote Similarity NPC473910
0.6949 Remote Similarity NPC475353
0.6949 Remote Similarity NPC477725
0.6949 Remote Similarity NPC474644
0.6949 Remote Similarity NPC477726
0.6949 Remote Similarity NPC473725
0.6949 Remote Similarity NPC317899
0.6949 Remote Similarity NPC473896
0.6935 Remote Similarity NPC6795
0.6923 Remote Similarity NPC149668
0.6885 Remote Similarity NPC469373
0.6875 Remote Similarity NPC475221
0.6863 Remote Similarity NPC329762
0.6863 Remote Similarity NPC103236
0.6863 Remote Similarity NPC27444
0.6842 Remote Similarity NPC473672
0.6842 Remote Similarity NPC477458
0.6842 Remote Similarity NPC474495
0.6833 Remote Similarity NPC477661
0.6833 Remote Similarity NPC470969
0.6833 Remote Similarity NPC473865
0.6833 Remote Similarity NPC325977
0.6833 Remote Similarity NPC473847
0.6833 Remote Similarity NPC474643
0.6833 Remote Similarity NPC470968
0.6833 Remote Similarity NPC475384
0.6833 Remote Similarity NPC161838
0.6833 Remote Similarity NPC471960
0.6833 Remote Similarity NPC470967
0.6833 Remote Similarity NPC470966
0.6825 Remote Similarity NPC475984
0.6825 Remote Similarity NPC113293
0.6818 Remote Similarity NPC49863
0.68 Remote Similarity NPC155880
0.68 Remote Similarity NPC92863
0.6792 Remote Similarity NPC116934
0.678 Remote Similarity NPC322461
0.6769 Remote Similarity NPC326268
0.6769 Remote Similarity NPC7940
0.6769 Remote Similarity NPC323477
0.6769 Remote Similarity NPC318420
0.6731 Remote Similarity NPC269823
0.6727 Remote Similarity NPC157096
0.6721 Remote Similarity NPC71755
0.6721 Remote Similarity NPC225929
0.6721 Remote Similarity NPC470970
0.6719 Remote Similarity NPC470965
0.6714 Remote Similarity NPC227396
0.6667 Remote Similarity NPC182840
0.6667 Remote Similarity NPC255042
0.6667 Remote Similarity NPC474391
0.6667 Remote Similarity NPC474913
0.6667 Remote Similarity NPC329686
0.6667 Remote Similarity NPC267514
0.6667 Remote Similarity NPC187315
0.6667 Remote Similarity NPC29091
0.6667 Remote Similarity NPC103213
0.6667 Remote Similarity NPC145755
0.6667 Remote Similarity NPC474460
0.6667 Remote Similarity NPC328653
0.662 Remote Similarity NPC260396
0.6615 Remote Similarity NPC476658
0.661 Remote Similarity NPC474496
0.6607 Remote Similarity NPC324812
0.6604 Remote Similarity NPC256766
0.6604 Remote Similarity NPC213538
0.6571 Remote Similarity NPC325627
0.6567 Remote Similarity NPC473752
0.6567 Remote Similarity NPC26500
0.6567 Remote Similarity NPC99619
0.6567 Remote Similarity NPC106613
0.6562 Remote Similarity NPC64985
0.6557 Remote Similarity NPC249645
0.6557 Remote Similarity NPC55412
0.6552 Remote Similarity NPC29234
0.6545 Remote Similarity NPC160628
0.6545 Remote Similarity NPC239754
0.6545 Remote Similarity NPC140501
0.6531 Remote Similarity NPC58957
0.6515 Remote Similarity NPC476657
0.6515 Remote Similarity NPC476655
0.6515 Remote Similarity NPC476654
0.6515 Remote Similarity NPC320642
0.6508 Remote Similarity NPC278202
0.65 Remote Similarity NPC137538
0.6471 Remote Similarity NPC309466

  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 NPC61177 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
0.7797 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4220 Pre-registration
0.6667 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6557 Remote Similarity NPD4219 Approved
0.6545 Remote Similarity NPD39 Approved
0.6545 Remote Similarity NPD4265 Approved
0.6346 Remote Similarity NPD5783 Phase 3
0.625 Remote Similarity NPD4222 Approved
0.6207 Remote Similarity NPD3173 Approved
0.6182 Remote Similarity NPD5326 Phase 3
0.6119 Remote Similarity NPD3197 Phase 1
0.6071 Remote Similarity NPD6097 Approved
0.6071 Remote Similarity NPD6096 Approved
0.6066 Remote Similarity NPD3172 Approved
0.6061 Remote Similarity NPD4194 Approved
0.6061 Remote Similarity NPD4191 Approved
0.6061 Remote Similarity NPD4193 Approved
0.6061 Remote Similarity NPD4192 Approved
0.6034 Remote Similarity NPD5343 Approved
0.6 Remote Similarity NPD6927 Phase 3
0.597 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5968 Remote Similarity NPD3195 Phase 2
0.5968 Remote Similarity NPD3194 Approved
0.5968 Remote Similarity NPD3196 Approved
0.5968 Remote Similarity NPD4266 Approved
0.5965 Remote Similarity NPD3174 Discontinued
0.5921 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5846 Remote Similarity NPD6109 Phase 1
0.5789 Remote Similarity NPD4756 Discovery
0.5769 Remote Similarity NPD4252 Approved
0.575 Remote Similarity NPD5331 Approved
0.575 Remote Similarity NPD5332 Approved
0.5738 Remote Similarity NPD28 Approved
0.5738 Remote Similarity NPD29 Approved
0.5714 Remote Similarity NPD4268 Approved
0.5714 Remote Similarity NPD539 Approved
0.5714 Remote Similarity NPD4271 Approved
0.5676 Remote Similarity NPD4732 Discontinued
0.5652 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4270 Approved
0.5625 Remote Similarity NPD342 Phase 1
0.5625 Remote Similarity NPD4269 Approved
0.5606 Remote Similarity NPD585 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