NPASS Compound

Natural Product: NPC609165

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 53 55 0 0 0 0 0 0 0 0999 V2000 1.0024 -2.4484 -2.4791 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3928 -1.4736 -1.8144 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3302 -0.4521 -2.5860 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2931 0.4040 -1.8239 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5268 -0.1391 -0.4413 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5746 0.5707 0.3182 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6914 -0.4014 0.7477 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3160 1.5675 -0.5919 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2989 2.2106 0.1986 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1817 1.3294 1.5276 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1269 0.7007 2.3737 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3968 -0.4248 1.7081 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1564 -0.2162 0.2485 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6034 1.0469 0.0284 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4546 -1.4568 -0.3157 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6004 -2.1235 0.2945 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9852 -1.7005 -0.0178 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4518 -0.3796 0.3598 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8983 0.6113 -0.3965 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2744 1.7917 0.3797 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0843 1.3930 1.7185 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5639 0.1083 1.7484 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2358 -0.5535 2.7505 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5599 -3.2476 -2.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9782 -2.5053 -3.5714 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3560 0.1610 -3.2243 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9424 -1.0151 -3.3606 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2646 0.4544 -2.3874 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8896 1.4557 -1.8237 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8548 -1.1965 -0.5645 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3273 -0.8635 1.6883 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8729 -1.1647 -0.0243 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5959 0.1890 1.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9175 1.0260 -1.3626 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6638 2.3460 -0.9816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5190 3.0571 -0.3013 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0992 1.4244 2.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9533 2.4206 1.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5219 0.3112 3.3362 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3914 1.4914 2.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9872 -1.3808 1.8156 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5376 -0.6035 2.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1471 1.0727 -0.9372 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1048 1.9390 -0.0840 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1994 1.3265 0.9087 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4288 -2.2605 -0.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4665 -2.2150 1.4411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5887 -3.2549 0.0487 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2224 -1.8134 -1.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7470 -2.4276 0.4393 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9777 0.5523 -1.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3128 2.1343 0.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5868 2.6220 0.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 6 8 1 0 8 9 1 0 6 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 15 2 1 0 22 18 1 0 13 5 1 0 1 24 1 0 1 25 1 0 3 26 1 0 3 27 1 0 4 28 1 0 4 29 1 0 5 30 1 6 7 31 1 0 7 32 1 0 7 33 1 0 8 34 1 0 8 35 1 0 9 36 1 0 10 37 1 0 10 38 1 0 11 39 1 0 11 40 1 0 12 41 1 0 12 42 1 0 14 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 16 47 1 0 16 48 1 0 17 49 1 0 17 50 1 0 19 51 1 0 20 52 1 0 20 53 1 0 M END

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

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 NPC609165 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	14280
0.1-0.2	28987
0.2-0.3	6089
0.3-0.4	352
0.4-0.5	104
0.5-0.6	26
0.6-0.7	11
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC106416
1.0	High Similarity	NPC86316
0.7308	Intermediate Similarity	NPC51486
0.717	Intermediate Similarity	NPC139692
0.7115	Intermediate Similarity	NPC200513
0.6923	Remote Similarity	NPC608380
0.6604	Remote Similarity	NPC476601
0.6327	Remote Similarity	NPC481631
0.6296	Remote Similarity	NPC251528
0.6275	Remote Similarity	NPC481628
0.625	Remote Similarity	NPC479457
0.62	Remote Similarity	NPC143765
0.6078	Remote Similarity	NPC69649
0.6061	Remote Similarity	NPC392
0.6061	Remote Similarity	NPC177524
0.6061	Remote Similarity	NPC219900
0.597	Remote Similarity	NPC479461
0.5965	Remote Similarity	NPC177037
0.5965	Remote Similarity	NPC472814
0.5932	Remote Similarity	NPC234993
0.5932	Remote Similarity	NPC134072
0.5882	Remote Similarity	NPC476406
0.5789	Remote Similarity	NPC174342
0.5636	Remote Similarity	NPC194322
0.5636	Remote Similarity	NPC488496
0.5636	Remote Similarity	NPC488504
0.5593	Remote Similarity	NPC65661
0.5577	Remote Similarity	NPC149680
0.5577	Remote Similarity	NPC600344
0.55	Remote Similarity	NPC600691
0.5455	Remote Similarity	NPC35655
0.5441	Remote Similarity	NPC599990
0.541	Remote Similarity	NPC242848
0.5286	Remote Similarity	NPC479455
0.5286	Remote Similarity	NPC479454
0.5254	Remote Similarity	NPC79027
0.5172	Remote Similarity	NPC12170
0.5167	Remote Similarity	NPC131813
0.5088	Remote Similarity	NPC4509
0.5085	Remote Similarity	NPC217394
0.5077	Remote Similarity	NPC487285
0.5077	Remote Similarity	NPC487284

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC609165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5835
0.1-0.2	3156
0.2-0.3	155
0.3-0.4	0
0.4-0.5	2
0.5-0.6	0
0.6-0.7	1
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7115	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6686	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