NPASS Compound

Natural Product: NPC591887

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 34 36 0 0 0 0 0 0 0 0999 V2000 4.7444 0.6507 0.8330 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6649 -0.4108 0.5575 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4582 0.1499 1.1149 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2293 0.3023 0.3415 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5033 1.2962 0.5875 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0045 -0.7453 -0.6383 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2332 -0.7453 -1.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4771 -0.8329 -0.6997 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0603 -2.0123 -0.1898 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1545 -1.7409 0.5029 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3512 -0.3956 0.4884 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3455 0.3850 1.0267 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3497 1.7501 0.8444 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3234 2.3195 0.1025 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3447 1.5365 -0.4242 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3351 0.1773 -0.2438 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2010 -0.7448 -1.5115 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4714 -0.5010 -0.9331 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4440 -0.3611 -1.7367 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8395 0.6963 1.9372 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3003 1.6273 0.4775 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6910 0.4352 0.3429 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9768 -1.3586 0.9863 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3973 0.4909 2.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0411 -1.7846 -0.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2544 0.1253 -2.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1857 -1.6795 -2.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6370 -2.9915 -0.3624 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8047 -2.3965 1.0064 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1276 -0.0825 1.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1379 2.3581 1.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3436 3.4133 -0.0365 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5561 1.9907 -1.0101 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0549 -0.9216 -2.5146 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 6 17 1 0 17 18 1 0 18 19 2 0 18 2 1 0 16 8 1 0 16 11 1 0 1 20 1 0 1 21 1 0 1 22 1 0 2 23 1 1 3 24 1 0 6 25 1 1 7 26 1 0 7 27 1 0 9 28 1 0 10 29 1 0 12 30 1 0 13 31 1 0 14 32 1 0 15 33 1 0 17 34 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 NPC591887 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	35717
0.1-0.2	12693
0.2-0.3	935
0.3-0.4	331
0.4-0.5	128
0.5-0.6	42
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC602670
0.7963	Intermediate Similarity	NPC474561
0.7797	Intermediate Similarity	NPC600670
0.7778	Intermediate Similarity	NPC606619
0.7778	Intermediate Similarity	NPC610347
0.7069	Intermediate Similarity	NPC603509
0.7069	Intermediate Similarity	NPC605537
0.6866	Remote Similarity	NPC601302
0.6866	Remote Similarity	NPC610128
0.6765	Remote Similarity	NPC605408
0.5915	Remote Similarity	NPC604280
0.5733	Remote Similarity	NPC601763
0.5676	Remote Similarity	NPC600013
0.5676	Remote Similarity	NPC601387
0.5676	Remote Similarity	NPC604088
0.5676	Remote Similarity	NPC605600
0.5658	Remote Similarity	NPC610080
0.5541	Remote Similarity	NPC602956
0.5517	Remote Similarity	NPC608269
0.5488	Remote Similarity	NPC473640
0.5397	Remote Similarity	NPC602969
0.537	Remote Similarity	NPC310665
0.5357	Remote Similarity	NPC55772
0.5357	Remote Similarity	NPC605643
0.5306	Remote Similarity	NPC601214
0.5303	Remote Similarity	NPC602245
0.5303	Remote Similarity	NPC606412
0.5263	Remote Similarity	NPC149155
0.5263	Remote Similarity	NPC203468
0.5263	Remote Similarity	NPC190296
0.5263	Remote Similarity	NPC110500
0.5263	Remote Similarity	NPC605329
0.5254	Remote Similarity	NPC200214
0.5244	Remote Similarity	NPC600277
0.5238	Remote Similarity	NPC601650
0.5224	Remote Similarity	NPC606618
0.5192	Remote Similarity	NPC279081
0.5185	Remote Similarity	NPC326845
0.5185	Remote Similarity	NPC603279
0.5179	Remote Similarity	NPC78020
0.5172	Remote Similarity	NPC480318
0.5167	Remote Similarity	NPC267885
0.5156	Remote Similarity	NPC611116
0.5152	Remote Similarity	NPC606272
0.5094	Remote Similarity	NPC29886
0.5088	Remote Similarity	NPC315555
0.5088	Remote Similarity	NPC59269
0.5088	Remote Similarity	NPC600736
0.5085	Remote Similarity	NPC248041
0.5079	Remote Similarity	NPC469760
0.5079	Remote Similarity	NPC469786
0.5077	Remote Similarity	NPC603162

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC591887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4926
0.1-0.2	4047
0.2-0.3	125
0.3-0.4	41
0.4-0.5	8
0.5-0.6	2
0.6-0.7	0
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	Drug ID	Developmental Stage
0.5263	Remote Similarity	NPD482	Phase 4
0.5172	Remote Similarity	NPD749	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