NPASS Compound

Natural Product: NPC611921

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 59 62 0 0 0 0 0 0 0 0999 V2000 6.2964 -0.7881 1.0709 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6086 0.0322 0.0713 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6448 -0.2034 -1.1533 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8703 1.1406 0.5095 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1950 1.9580 -0.3934 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0781 1.3570 -1.1031 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7455 1.9662 -2.1807 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2483 0.2028 -0.8483 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7681 -0.3616 -2.0511 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6751 -0.8198 0.1509 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3605 -1.5110 0.5946 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3308 -0.7042 -0.0384 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0065 -0.5891 0.6326 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4519 -1.9261 1.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9309 -2.1293 1.1646 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6771 -1.4194 0.1014 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5811 -1.9885 -0.6704 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3053 -1.2840 -1.7088 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1668 -1.8421 -2.4383 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0056 0.1259 -1.8954 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1054 0.6922 -1.1265 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3525 0.0225 -0.0688 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6185 0.6692 1.2761 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8887 0.0396 -0.4177 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4015 1.3850 -0.8192 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7782 2.3683 0.1024 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0564 1.4323 -1.1482 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9004 0.6725 -0.1951 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1788 1.4212 1.0455 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8466 -0.1857 1.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0324 -1.4786 0.6069 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5344 -1.4512 1.5619 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9037 2.8832 0.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9190 2.3941 -1.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1851 0.1053 -2.8266 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2840 -1.6091 -0.3094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1374 -0.3722 1.0593 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3503 -2.5676 0.2539 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3362 -1.5590 1.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1583 -1.0930 -1.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9086 0.1107 1.4836 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0521 -2.0837 2.1298 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9573 -2.7011 0.4676 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3581 -1.8394 2.1397 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1347 -3.2171 1.0478 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8053 -3.0428 -0.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5343 0.6792 -2.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9106 1.7379 -1.2929 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2001 1.6016 1.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2125 0.0038 1.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7228 0.9515 1.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7876 -0.6262 -1.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9383 1.6582 -1.7764 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1561 3.1647 -0.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2063 1.0213 -2.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4002 2.4853 -1.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7992 0.9444 1.7980 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6509 2.4042 0.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2472 1.7627 1.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 6 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 1 28 8 1 0 28 12 1 0 24 13 1 0 22 16 1 0 1 30 1 0 1 31 1 0 1 32 1 0 5 33 1 0 5 34 1 0 9 35 1 0 10 36 1 0 10 37 1 0 11 38 1 0 11 39 1 0 12 40 1 6 13 41 1 1 14 42 1 0 14 43 1 0 15 44 1 0 15 45 1 0 17 46 1 0 20 47 1 0 21 48 1 0 23 49 1 0 23 50 1 0 23 51 1 0 24 52 1 6 25 53 1 6 26 54 1 0 27 55 1 0 27 56 1 0 29 57 1 0 29 58 1 0 29 59 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 NPC611921 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	17749
0.1-0.2	28529
0.2-0.3	3514
0.3-0.4	48
0.4-0.5	9
0.5-0.6	6
0.6-0.7	0
0.7-0.8	2
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	NPC44063
0.75	Intermediate Similarity	NPC334061
0.5733	Remote Similarity	NPC488911
0.5694	Remote Similarity	NPC478926
0.5658	Remote Similarity	NPC482048
0.5362	Remote Similarity	NPC144956
0.5143	Remote Similarity	NPC169375
0.5132	Remote Similarity	NPC2766

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC611921 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6341
0.1-0.2	2545
0.2-0.3	154
0.3-0.4	62
0.4-0.5	10
0.5-0.6	21
0.6-0.7	7
0.7-0.8	2
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD5697	Phase 4
0.8983	High Similarity	NPD6899	Phase 4
0.8361	Intermediate Similarity	NPD4729	Approved
0.8226	Intermediate Similarity	NPD4730	Phase 4
0.7681	Intermediate Similarity	NPD8297	Phase 4
0.75	Intermediate Similarity	NPD4696	Phase 4
0.6923	Remote Similarity	NPD5739	Phase 4
0.6818	Remote Similarity	NPD4632	Approved
0.6456	Remote Similarity	NPD7057	Phase 3
0.6456	Remote Similarity	NPD7058	Phase 2
0.6386	Remote Similarity	NPD7962	Phase 2
0.6375	Remote Similarity	NPD7239	Suspended
0.6	Remote Similarity	NPD6649	Approved
0.5921	Remote Similarity	NPD6650	Phase 4
0.589	Remote Similarity	NPD7320	Phase 4
0.5821	Remote Similarity	NPD5211	Phase 2
0.5775	Remote Similarity	NPD4767	Approved
0.5733	Remote Similarity	NPD6372	Approved
0.5694	Remote Similarity	NPD4768	Phase 4
0.5658	Remote Similarity	NPD6373	Phase 4
0.5658	Remote Similarity	NPD6909	Phase 4
0.56	Remote Similarity	NPD6882	Phase 4
0.5584	Remote Similarity	NPD6908	Approved
0.5526	Remote Similarity	NPD6333	Approved
0.5526	Remote Similarity	NPD6334	Phase 4
0.5493	Remote Similarity	NPD5696	Phase 4
0.5362	Remote Similarity	NPD5286	Phase 4
0.5294	Remote Similarity	NPD6079	Phase 4
0.5231	Remote Similarity	NPD4195	Phase 4
0.5217	Remote Similarity	NPD4629	Phase 4
0.5211	Remote Similarity	NPD4633	Phase 4
0.5132	Remote Similarity	NPD5983	Phase 2
0.5067	Remote Similarity	NPD6012	Phase 4
0.5063	Remote Similarity	NPD6009	Phase 4

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