Natural Product: NPC91461

Natural Product IDNPC91461
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 (+)-Hannokinol
IUPAC Name (3R,5R)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol
Synonyms (+)-Hannokinol
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL474475
PubChem CID 11034432
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002650] Diarylheptanoids
        • [CHEMONTID:0002651] Linear diarylheptanoids
          • [CHEMONTID:0000356] Curcuminoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey GZVIQGVWSNEONZ-RTBURBONSA-N
Standard InCHI InChI=1S/C19H24O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-4,7-10,18-23H,5-6,11-13H2/t18-,19-/m1/s1
SMILES c1cc(ccc1CC[C@H](C[C@@H](CCc1ccc(cc1)O)O)O)O

  Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np100392m]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota rhizomes SiMao City, Yunnan Province, China 1996-OCT PMID[11908966]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota Rhizomes n.a. n.a. PMID[12350150]
NPO7863 Dioscorea opposita Species Dioscoreaceae Eukaryota aerial parts n.a. n.a. PMID[16124773]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota rhizomes Kampaengsaen district, Nakhon Pathom province, Thailand n.a. PMID[18554915]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota aerial parts n.a. n.a. PMID[20196571]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[20715765]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO32876 alnus hirsuta f. sibirica Species Betulaceae Eukaryota n.a. n.a. n.a. PMID[23465614]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23910596]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[33253561]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8176399]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO32876 alnus hirsuta f. sibirica Species Betulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7863 Dioscorea opposita Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13332 Tacca chantrieri Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7863 Dioscorea opposita Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7863 Dioscorea opposita Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7863 Dioscorea opposita Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22901 Curcuma comosa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13332 Tacca chantrieri Species Taccaceae 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 Organism Name 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

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT324 Individual protein Cyclooxygenase-1 Ovis aries IC50 > 100.0 ug.mL-1 PMID[19303782]
NPT325 Individual protein Cyclooxygenase-2 Ovis aries IC50 > 100.0 ug.mL-1 PMID[19303782]
NPT43 Individual protein Tyrosinase Agaricus bisporus Inhibition < 17.0 % PMID[23910596]

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell line HL-60 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[11908966]
NPT924 Cell line HSC-2 Homo sapiens IC50 = 231.0 ug.mL-1 PMID[11908966]
NPT113 Cell line RAW264.7 Mus musculus IC50 > 100000.0 nM PMID[21807513]
NPT520 Cell line 3T3-L1 Mus musculus Activity = 61.2 % PMID[23465614]
NPT520 Cell line 3T3-L1 Mus musculus Activity = 90.2 % PMID[23465614]
NPT34 Cell line BV-2 Mus musculus Activity = 94.8 % PMID[33253561]
NPT34 Cell line BV-2 Mus musculus Activity = 101.9 % PMID[33253561]
NPT34 Cell line BV-2 Mus musculus Inhibition = 51.3 % PMID[33422907]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 > 100.0 ug.mL-1 PMID[19303782]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[23910596]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 21.9 % PMID[23910596]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 23.1 % PMID[23910596]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 15.7 % PMID[23910596]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 20.3 % PMID[23910596]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. Inhibition = 22.0 % PMID[23910596]
NPT1 Others Radical scavenging activity n.a. IC50 > 100.0 ug.mL-1 PMID[19303782]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC91461 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC7686
1.0 High Similarity NPC40258
0.871 High Similarity NPC213730
0.8182 Intermediate Similarity NPC179002
0.8182 Intermediate Similarity NPC257430
0.7333 Intermediate Similarity NPC138117
0.7333 Intermediate Similarity NPC325292
0.697 Remote Similarity NPC187583
0.6923 Remote Similarity NPC186843
0.6857 Remote Similarity NPC132078
0.6857 Remote Similarity NPC600556
0.675 Remote Similarity NPC473853
0.675 Remote Similarity NPC470212
0.6452 Remote Similarity NPC322515
0.6452 Remote Similarity NPC121478
0.6316 Remote Similarity NPC177576
0.6279 Remote Similarity NPC470213
0.6 Remote Similarity NPC608485
0.5854 Remote Similarity NPC216468
0.5854 Remote Similarity NPC226401
0.5854 Remote Similarity NPC78119
0.5854 Remote Similarity NPC174096
0.575 Remote Similarity NPC312675
0.575 Remote Similarity NPC262156
0.575 Remote Similarity NPC184651
0.575 Remote Similarity NPC113865
0.5714 Remote Similarity NPC321252
0.5714 Remote Similarity NPC252544
0.5625 Remote Similarity NPC23167
0.5556 Remote Similarity NPC25689
0.5476 Remote Similarity NPC249435
0.5455 Remote Similarity NPC285350
0.5455 Remote Similarity NPC265454
0.5455 Remote Similarity NPC324571
0.5455 Remote Similarity NPC51333
0.5455 Remote Similarity NPC63345
0.5405 Remote Similarity NPC474272
0.5333 Remote Similarity NPC485986
0.5294 Remote Similarity NPC242240
0.5227 Remote Similarity NPC98631
0.5227 Remote Similarity NPC206615
0.5208 Remote Similarity NPC310718
0.5143 Remote Similarity NPC260000

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC91461 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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