NPASS Compound

Natural Product: NPC609181

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 38 40 0 0 0 0 0 0 0 0999 V2000 -4.5315 0.5881 -1.4604 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2902 0.3404 -0.6977 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8333 1.3273 0.1562 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4872 2.5345 0.3267 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6711 1.1278 0.8876 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1306 2.1338 1.8119 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0061 -0.0659 0.7323 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4669 -1.0595 -0.1279 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6189 -0.8506 -0.8470 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1134 -1.8128 -1.7148 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7258 -2.2945 -0.2503 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2277 -3.2775 -0.8531 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6110 -2.4384 0.3143 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1112 -1.2862 1.0981 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3082 -0.6422 0.4786 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1973 0.3269 -0.4971 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3010 0.9257 -1.0734 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5768 0.5615 -0.6789 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6946 1.1687 -1.2634 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7085 -0.3929 0.2824 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6037 -0.9875 0.8545 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1456 -0.3241 1.4249 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6063 -0.0649 -2.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3775 0.5051 -0.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4862 1.6408 -1.8329 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0831 3.3561 -0.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3020 2.7320 1.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7309 1.6605 2.7557 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9226 2.8340 2.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8747 -2.4326 -1.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3206 -2.6161 -0.5345 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6337 -3.4040 0.8968 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4809 -1.6870 2.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1895 0.6073 -0.8014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2026 1.6925 -1.8456 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0270 2.0193 -0.7910 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6905 -0.6981 0.6110 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6833 -1.7479 1.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 1 0 5 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 8 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 14 22 1 0 9 2 1 0 21 15 1 0 22 7 1 0 1 23 1 0 1 24 1 0 1 25 1 0 4 26 1 0 6 27 1 0 6 28 1 0 6 29 1 0 10 30 1 0 13 31 1 0 13 32 1 0 14 33 1 1 16 34 1 0 17 35 1 0 19 36 1 0 20 37 1 0 21 38 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 NPC609181 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	24669
0.1-0.2	21482
0.2-0.3	3118
0.3-0.4	378
0.4-0.5	160
0.5-0.6	30
0.6-0.7	9
0.7-0.8	1
0.8-0.85	1
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	NPC167624
1.0	High Similarity	NPC166482
0.8043	Intermediate Similarity	NPC248372
0.7917	Intermediate Similarity	NPC192083
0.7708	Intermediate Similarity	NPC296917
0.7708	Intermediate Similarity	NPC170907
0.7551	Intermediate Similarity	NPC485881
0.7292	Intermediate Similarity	NPC603284
0.6863	Remote Similarity	NPC324134
0.6863	Remote Similarity	NPC480995
0.6863	Remote Similarity	NPC40833
0.6863	Remote Similarity	NPC477503
0.6667	Remote Similarity	NPC270789
0.6667	Remote Similarity	NPC324386
0.6346	Remote Similarity	NPC110776
0.6182	Remote Similarity	NPC231134
0.6038	Remote Similarity	NPC110038
0.5818	Remote Similarity	NPC2416
0.5769	Remote Similarity	NPC213322
0.5763	Remote Similarity	NPC265040
0.5686	Remote Similarity	NPC329225
0.5686	Remote Similarity	NPC147686
0.566	Remote Similarity	NPC32441
0.566	Remote Similarity	NPC79943
0.5536	Remote Similarity	NPC271590
0.5472	Remote Similarity	NPC225153
0.5472	Remote Similarity	NPC479876
0.5455	Remote Similarity	NPC300668
0.5455	Remote Similarity	NPC215885
0.5455	Remote Similarity	NPC329203
0.5455	Remote Similarity	NPC222342
0.5424	Remote Similarity	NPC480991
0.5357	Remote Similarity	NPC469764
0.5357	Remote Similarity	NPC480992
0.5357	Remote Similarity	NPC475267
0.5357	Remote Similarity	NPC606248
0.5333	Remote Similarity	NPC107572
0.5333	Remote Similarity	NPC32739
0.5312	Remote Similarity	NPC473078
0.5286	Remote Similarity	NPC483810
0.5273	Remote Similarity	NPC312391
0.5167	Remote Similarity	NPC164980
0.5161	Remote Similarity	NPC470133
0.5161	Remote Similarity	NPC220998
0.5152	Remote Similarity	NPC246948
0.5152	Remote Similarity	NPC142405
0.5088	Remote Similarity	NPC476153

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC609181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3799
0.1-0.2	5219
0.2-0.3	124
0.3-0.4	4
0.4-0.5	1
0.5-0.6	2
0.6-0.7	0
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
0.7917	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD1549	Phase 2
0.566	Remote Similarity	NPD1552	Clinical (unspecified phase)

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