Structure

Physi-Chem Properties

Molecular Weight:  222.2
Volume:  251.117
LogP:  4.474
LogD:  3.975
LogS:  -4.801
# Rotatable Bonds:  0
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.662
Synthetic Accessibility Score:  5.086
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.7
MDCK Permeability:  1.3933986338088289e-05
Pgp-inhibitor:  0.046
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.42

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.847
Plasma Protein Binding (PPB):  91.7713394165039%
Volume Distribution (VD):  1.308
Pgp-substrate:  13.463842391967773%

ADMET: Metabolism

CYP1A2-inhibitor:  0.054
CYP1A2-substrate:  0.488
CYP2C19-inhibitor:  0.148
CYP2C19-substrate:  0.882
CYP2C9-inhibitor:  0.155
CYP2C9-substrate:  0.72
CYP2D6-inhibitor:  0.031
CYP2D6-substrate:  0.464
CYP3A4-inhibitor:  0.588
CYP3A4-substrate:  0.18

ADMET: Excretion

Clearance (CL):  13.794
Half-life (T1/2):  0.089

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.373
Drug-inuced Liver Injury (DILI):  0.049
AMES Toxicity:  0.022
Rat Oral Acute Toxicity:  0.05
Maximum Recommended Daily Dose:  0.16
Skin Sensitization:  0.714
Carcinogencity:  0.058
Eye Corrosion:  0.029
Eye Irritation:  0.169
Respiratory Toxicity:  0.614

Download Data

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

  Natural Product: NPC294858

Natural Product ID:  NPC294858
Common Name*:   Beta-Caryophyllene Alcohol
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  FUQAYSQLAOJBBC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3
SMILES:  CC1(C)CC2C1CCC1(C)CCCC2(C1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1374805
PubChem CID:   61125
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001670] Tertiary 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
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4039(01)00209-X]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[10575373]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. leaf n.a. PMID[15467205]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. whole plant n.a. PMID[16808005]
NPO28807 Laggera pterodonta Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[20506820]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23102654]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[31103896]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. Database[FooDB]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28928 Piper nigrum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28807 Laggera pterodonta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28807 Laggera pterodonta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28928 Piper nigrum Species Piperaceae 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
NPT442 Individual Protein Ferritin light chain Equus caballus Potency = 35481.3 nM PMID[571102]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 50118.7 nM PMID[571102]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 22387.2 nM PMID[571102]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 117.35 % PMID[571103]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 113.02 % PMID[571103]

☑ 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 NPC294858 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
0.8333 Intermediate Similarity NPC475515
0.8333 Intermediate Similarity NPC215671
0.8333 Intermediate Similarity NPC87296
0.7959 Intermediate Similarity NPC14552
0.7925 Intermediate Similarity NPC53209
0.7736 Intermediate Similarity NPC102336
0.7736 Intermediate Similarity NPC36002
0.7647 Intermediate Similarity NPC95969
0.7647 Intermediate Similarity NPC127997
0.7551 Intermediate Similarity NPC313795
0.7455 Intermediate Similarity NPC471269
0.74 Intermediate Similarity NPC77550
0.74 Intermediate Similarity NPC108441
0.7333 Intermediate Similarity NPC328441
0.7321 Intermediate Similarity NPC3025
0.7273 Intermediate Similarity NPC32222
0.7273 Intermediate Similarity NPC202146
0.7255 Intermediate Similarity NPC198540
0.7255 Intermediate Similarity NPC223468
0.7255 Intermediate Similarity NPC147343
0.7255 Intermediate Similarity NPC287550
0.7255 Intermediate Similarity NPC84030
0.7255 Intermediate Similarity NPC176309
0.7193 Intermediate Similarity NPC135438
0.7193 Intermediate Similarity NPC236588
0.7143 Intermediate Similarity NPC300189
0.7091 Intermediate Similarity NPC161473
0.7069 Intermediate Similarity NPC474769
0.7069 Intermediate Similarity NPC189290
0.7018 Intermediate Similarity NPC39068
0.7018 Intermediate Similarity NPC264779
0.7 Intermediate Similarity NPC144891
0.6981 Remote Similarity NPC316035
0.6949 Remote Similarity NPC95958
0.6935 Remote Similarity NPC80463
0.6842 Remote Similarity NPC45387
0.6833 Remote Similarity NPC475412
0.678 Remote Similarity NPC162685
0.6727 Remote Similarity NPC307022
0.6724 Remote Similarity NPC179024
0.6721 Remote Similarity NPC95804
0.6721 Remote Similarity NPC185547
0.661 Remote Similarity NPC291147
0.6562 Remote Similarity NPC475897
0.6562 Remote Similarity NPC473929
0.6552 Remote Similarity NPC218525
0.6508 Remote Similarity NPC101128
0.65 Remote Similarity NPC47663
0.6458 Remote Similarity NPC177022
0.6452 Remote Similarity NPC71460
0.6452 Remote Similarity NPC148174
0.6452 Remote Similarity NPC218585
0.6452 Remote Similarity NPC41160
0.6452 Remote Similarity NPC475807
0.6406 Remote Similarity NPC64123
0.6406 Remote Similarity NPC258595
0.6406 Remote Similarity NPC260116
0.6406 Remote Similarity NPC230047
0.6406 Remote Similarity NPC19311
0.64 Remote Similarity NPC469759
0.64 Remote Similarity NPC160261
0.6393 Remote Similarity NPC99480
0.6393 Remote Similarity NPC475968
0.6393 Remote Similarity NPC184049
0.6379 Remote Similarity NPC286752
0.6364 Remote Similarity NPC478228
0.6349 Remote Similarity NPC290791
0.6349 Remote Similarity NPC292419
0.6349 Remote Similarity NPC81615
0.6349 Remote Similarity NPC114891
0.6346 Remote Similarity NPC302939
0.6346 Remote Similarity NPC287331
0.6333 Remote Similarity NPC29976
0.6333 Remote Similarity NPC150713
0.629 Remote Similarity NPC135648
0.6271 Remote Similarity NPC89069
0.6271 Remote Similarity NPC178223
0.6271 Remote Similarity NPC283655
0.6271 Remote Similarity NPC277917
0.6271 Remote Similarity NPC166894
0.625 Remote Similarity NPC118937
0.625 Remote Similarity NPC128608
0.625 Remote Similarity NPC68656
0.625 Remote Similarity NPC69149
0.625 Remote Similarity NPC281540
0.625 Remote Similarity NPC61665
0.625 Remote Similarity NPC144650
0.625 Remote Similarity NPC159654
0.625 Remote Similarity NPC219940
0.625 Remote Similarity NPC167995
0.6232 Remote Similarity NPC476422
0.623 Remote Similarity NPC476735
0.6212 Remote Similarity NPC101307
0.6212 Remote Similarity NPC185874
0.6212 Remote Similarity NPC139207
0.6212 Remote Similarity NPC63190
0.6212 Remote Similarity NPC269077
0.6212 Remote Similarity NPC263161
0.6212 Remote Similarity NPC48079
0.6212 Remote Similarity NPC88454
0.6212 Remote Similarity NPC117607
0.6212 Remote Similarity NPC476928
0.6212 Remote Similarity NPC41542
0.6212 Remote Similarity NPC253303
0.6207 Remote Similarity NPC192962
0.62 Remote Similarity NPC221022
0.619 Remote Similarity NPC194208
0.619 Remote Similarity NPC15152
0.619 Remote Similarity NPC282694
0.619 Remote Similarity NPC79576
0.6182 Remote Similarity NPC314087
0.6182 Remote Similarity NPC100445
0.6167 Remote Similarity NPC274396
0.6154 Remote Similarity NPC208198
0.6154 Remote Similarity NPC472946
0.6154 Remote Similarity NPC243469
0.6154 Remote Similarity NPC41577
0.6154 Remote Similarity NPC172613
0.6154 Remote Similarity NPC190827
0.6154 Remote Similarity NPC473276
0.6154 Remote Similarity NPC60837
0.6154 Remote Similarity NPC11555
0.6154 Remote Similarity NPC474380
0.6154 Remote Similarity NPC282619
0.6154 Remote Similarity NPC2728
0.6154 Remote Similarity NPC475943
0.6143 Remote Similarity NPC74639
0.6129 Remote Similarity NPC185116
0.6119 Remote Similarity NPC244790
0.6119 Remote Similarity NPC2648
0.6119 Remote Similarity NPC94192
0.6119 Remote Similarity NPC472741
0.6119 Remote Similarity NPC276616
0.6119 Remote Similarity NPC475893
0.6119 Remote Similarity NPC474756
0.6119 Remote Similarity NPC245795
0.6094 Remote Similarity NPC209686
0.6094 Remote Similarity NPC249078
0.6094 Remote Similarity NPC236099
0.6087 Remote Similarity NPC478227
0.6066 Remote Similarity NPC119425
0.6061 Remote Similarity NPC279434
0.6061 Remote Similarity NPC44122
0.6061 Remote Similarity NPC142712
0.6061 Remote Similarity NPC103734
0.6061 Remote Similarity NPC476406
0.6056 Remote Similarity NPC139765
0.6056 Remote Similarity NPC131584
0.6032 Remote Similarity NPC478126
0.6029 Remote Similarity NPC9942
0.6029 Remote Similarity NPC474248
0.6029 Remote Similarity NPC299948
0.6029 Remote Similarity NPC107919
0.6029 Remote Similarity NPC196197
0.6029 Remote Similarity NPC470830
0.6029 Remote Similarity NPC210323
0.6029 Remote Similarity NPC241085
0.6029 Remote Similarity NPC476431
0.6029 Remote Similarity NPC254037
0.6029 Remote Similarity NPC129829
0.6029 Remote Similarity NPC470833
0.6029 Remote Similarity NPC66407
0.6 Remote Similarity NPC94897
0.6 Remote Similarity NPC67508
0.6 Remote Similarity NPC199937
0.6 Remote Similarity NPC225415
0.6 Remote Similarity NPC84824
0.597 Remote Similarity NPC171225
0.597 Remote Similarity NPC473230
0.597 Remote Similarity NPC204233
0.597 Remote Similarity NPC472984
0.597 Remote Similarity NPC475884
0.5968 Remote Similarity NPC10017
0.5965 Remote Similarity NPC131623
0.5942 Remote Similarity NPC163020
0.5942 Remote Similarity NPC192192
0.5942 Remote Similarity NPC282454
0.5942 Remote Similarity NPC231945
0.5942 Remote Similarity NPC283316
0.5938 Remote Similarity NPC147524
0.5926 Remote Similarity NPC240994
0.5909 Remote Similarity NPC165069
0.5909 Remote Similarity NPC300442
0.5909 Remote Similarity NPC469791
0.5882 Remote Similarity NPC469987
0.5882 Remote Similarity NPC473225
0.5882 Remote Similarity NPC471238
0.5873 Remote Similarity NPC5698
0.5873 Remote Similarity NPC52431
0.5873 Remote Similarity NPC310228
0.5862 Remote Similarity NPC291724
0.5862 Remote Similarity NPC274261
0.5857 Remote Similarity NPC247195
0.5857 Remote Similarity NPC164022
0.5857 Remote Similarity NPC477792
0.5857 Remote Similarity NPC109457
0.5857 Remote Similarity NPC471272
0.5857 Remote Similarity NPC1340
0.5857 Remote Similarity NPC187471
0.5857 Remote Similarity NPC167706

  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 NPC294858 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
0.74 Intermediate Similarity NPD388 Approved
0.74 Intermediate Similarity NPD386 Approved
0.7255 Intermediate Similarity NPD385 Approved
0.7255 Intermediate Similarity NPD384 Approved
0.6346 Remote Similarity NPD367 Approved
0.6119 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6119 Remote Similarity NPD5360 Phase 3
0.6029 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5942 Remote Similarity NPD4787 Phase 1
0.5909 Remote Similarity NPD3171 Clinical (unspecified phase)
0.5857 Remote Similarity NPD4758 Discontinued
0.5833 Remote Similarity NPD615 Clinical (unspecified phase)
0.5821 Remote Similarity NPD4224 Phase 2
0.5797 Remote Similarity NPD3699 Clinical (unspecified phase)
0.5797 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5758 Remote Similarity NPD371 Approved
0.5634 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5634 Remote Similarity NPD4243 Approved
0.5634 Remote Similarity NPD4809 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