NPASS Compound

Natural Product: NPC29017

Natural Product ID	NPC29017
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JEJREKXHLFEVHN-VJDHNPKBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000472] Hydroxy acids and derivatives [CHEMONTID:0001713] Beta hydroxy acids and derivatives

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

Chemical Representations

RDKit 3D 44 47 0 0 0 0 0 0 0 0999 V2000 4.9826 -0.4233 -0.7584 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6453 -0.1943 -0.3591 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4320 -0.0667 1.0500 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9613 -0.2250 1.3780 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1804 -0.2514 0.0731 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5327 0.9036 -0.8109 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0440 0.9983 -0.8892 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5217 2.0842 0.0640 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7990 1.3695 1.3796 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7686 2.0066 0.6256 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1895 -0.4289 0.2752 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9393 -1.5032 -0.0956 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3671 -2.4498 -0.6829 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3888 -1.4964 0.2145 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5223 -1.5003 1.7418 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8420 -1.6249 2.1350 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1279 -0.3514 -0.3043 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3513 -0.6186 -0.9309 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1399 0.3701 -1.4581 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7491 1.6833 -1.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5481 1.9561 -0.7743 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7542 0.9501 -0.2424 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9022 -2.7079 -0.2573 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5915 0.4788 -0.9403 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5025 -0.9978 0.0359 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9781 -1.0823 -1.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0548 -0.7585 1.6624 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5715 0.6202 1.9766 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7952 -1.1926 1.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5422 -1.1756 -0.4587 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1634 1.8764 -0.4360 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1612 0.6796 -1.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 1.1751 -1.9231 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9881 3.0456 0.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3599 1.8292 2.2639 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0224 -0.6064 2.1459 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9649 -2.4087 2.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3656 -2.1513 1.4962 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7142 -1.6371 -1.0170 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0878 0.1075 -1.9376 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3899 2.4399 -1.8118 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2397 3.0032 -0.7205 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8344 1.2086 0.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5363 -2.9339 -1.1469 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 5 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 14 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 14 23 1 6 7 2 1 0 10 8 1 0 22 17 1 0 9 3 1 0 1 24 1 0 1 25 1 0 1 26 1 0 3 27 1 1 4 28 1 0 4 29 1 0 5 30 1 6 6 31 1 0 6 32 1 0 7 33 1 6 8 34 1 1 9 35 1 1 15 36 1 0 15 37 1 0 16 38 1 0 18 39 1 0 19 40 1 0 20 41 1 0 21 42 1 0 22 43 1 0 23 44 1 0 M END

Standard InCHIKey	JEJREKXHLFEVHN-VJDHNPKBSA-N
Standard InCHI	InChI=1S/C17H21NO5/c1-18-12-7-11(8-13(18)15-14(12)23-15)22-16(20)17(21,9-19)10-5-3-2-4-6-10/h2-6,11-15,19,21H,7-9H2,1H3/t11-,12-,13+,14-,15+,17-/m1/s1
SMILES	CN1[C@@H]2C[C@H](C[C@H]1[C@H]1[C@@H]2O1)OC(=O)[C@@](CO)(c1ccccc1)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
NPO25770	Dioncophyllum thollonii	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26320	Acer palmatum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28346	Phacelia minor	Species	Hydrophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26107	Montanoa speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26320	Acer palmatum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25770	Dioncophyllum thollonii	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14522	Uvaria cuneifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25950	Pinus apacheca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26452	Dermophis mexicanus	Species	Dermophiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26407	Deguelia rufescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13054	Rhamnus davurica	Species	Rhamnaceae	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

In vitro activity

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

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

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 NPC29017 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	18515
0.1-0.2	30445
0.2-0.3	870
0.3-0.4	18
0.4-0.5	8
0.5-0.6	0
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6731	Remote Similarity	NPC245836
0.6731	Remote Similarity	NPC233910
0.6731	Remote Similarity	NPC39830

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC29017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3297
0.1-0.2	5528
0.2-0.3	281
0.3-0.4	29
0.4-0.5	8
0.5-0.6	0
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2575	Phase 3
0.6731	Remote Similarity	NPD2570	Phase 4
0.6731	Remote Similarity	NPD2571	Approved
0.6731	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2573	Approved
0.6731	Remote Similarity	NPD2574	Discontinued
0.6604	Remote Similarity	NPD2566	Approved

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