NPASS Compound

Natural Product: NPC605943

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 88 92 0 0 0 0 0 0 0 0999 V2000 -4.5836 6.6728 1.1362 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0318 5.3514 1.2497 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2408 4.2749 0.9076 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9611 4.3880 0.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2196 3.2702 0.1051 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7426 1.9860 0.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8839 0.8644 -0.0354 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5551 1.0983 0.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3561 0.2293 -0.1772 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7205 0.5530 -0.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0346 1.9573 0.2317 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7966 2.2128 1.6662 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7348 2.7114 2.4415 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0951 3.0483 1.9253 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4683 2.9865 3.8888 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7023 -0.3781 -0.3013 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0305 -0.0797 -0.2048 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1024 -0.9012 -0.4931 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5306 -1.5941 0.6707 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2332 -2.7382 0.2607 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9446 -3.4354 1.3915 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6322 -4.5741 0.9128 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1371 -2.4317 -0.9063 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6265 -2.9284 -2.0804 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5069 -0.9876 -1.0257 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3324 -0.5811 0.0355 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2633 -0.1218 -1.0285 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0149 0.3145 -2.3351 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3052 -1.6555 -0.6314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9772 -2.0084 -0.7380 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5349 -3.2728 -1.0657 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0030 -1.0493 -0.5055 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3272 -1.3501 -0.5955 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7131 -2.4885 -0.8890 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3566 -0.3667 -0.3564 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5600 -0.8000 -0.4935 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7758 -1.2386 -0.6270 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7999 -2.6800 -0.7675 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9172 -3.1787 -1.3246 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1813 -4.5321 -0.6169 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1885 -2.4136 -1.1960 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0383 -2.8731 -2.2339 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0768 -0.9364 -1.3270 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2908 -0.3338 -0.0767 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6110 -0.6347 -1.6934 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5175 0.7386 -1.7244 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0013 1.8929 0.7138 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7695 3.0252 1.0512 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7406 7.0991 0.1377 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5180 6.8257 1.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1571 7.3275 1.8492 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5664 5.3788 0.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2069 3.4446 -0.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4747 2.6595 -0.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1111 2.1840 0.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8210 1.9934 2.1359 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6689 2.1996 1.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7019 3.5485 2.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9066 3.7454 1.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4808 4.1024 4.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2538 2.5821 4.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4783 2.5937 4.2021 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8256 -1.6785 -1.2655 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4436 -3.4325 -0.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7024 -2.7832 1.8532 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2328 -3.7845 2.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0417 -4.9956 0.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0959 -2.9785 -0.6957 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6470 -2.2421 -2.8025 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0370 -0.8354 -1.9785 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8632 -1.3475 0.3455 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4156 0.7453 -0.3438 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0959 1.2981 -2.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0495 -2.4124 -0.8105 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4555 -3.9634 -0.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3506 -1.1555 0.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7335 -3.4994 -2.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7846 -5.1548 -1.2763 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2216 -4.9775 -0.2920 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7861 -4.2678 0.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7556 -2.7100 -0.2611 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9758 -3.8604 -2.3153 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7671 -0.5419 -2.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1962 0.0515 -0.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4072 -1.0489 -2.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1237 1.0425 -2.5935 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4921 0.9453 0.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7539 2.8912 1.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 3 13 14 1 0 13 15 1 0 10 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 16 29 2 0 29 30 1 0 30 31 1 0 30 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 6 47 1 0 47 48 2 0 48 3 1 0 35 7 2 0 45 37 1 0 32 9 1 0 27 18 1 0 1 49 1 0 1 50 1 0 1 51 1 0 4 52 1 0 5 53 1 0 11 54 1 0 11 55 1 0 12 56 1 0 14 57 1 0 14 58 1 0 14 59 1 0 15 60 1 0 15 61 1 0 15 62 1 0 18 63 1 6 20 64 1 6 21 65 1 0 21 66 1 0 22 67 1 0 23 68 1 1 24 69 1 0 25 70 1 6 26 71 1 0 27 72 1 1 28 73 1 0 29 74 1 0 31 75 1 0 37 76 1 1 39 77 1 6 40 78 1 0 40 79 1 0 40 80 1 0 41 81 1 1 42 82 1 0 43 83 1 6 44 84 1 0 45 85 1 6 46 86 1 0 47 87 1 0 48 88 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 NPC605943 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	12174
0.1-0.2	32437
0.2-0.3	4056
0.3-0.4	875
0.4-0.5	254
0.5-0.6	45
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	Natural Product ID
1.0	High Similarity	NPC5319
0.7556	Intermediate Similarity	NPC131745
0.7303	Intermediate Similarity	NPC278419
0.7303	Intermediate Similarity	NPC179198
0.617	Remote Similarity	NPC66087
0.6111	Remote Similarity	NPC289667
0.6087	Remote Similarity	NPC472459
0.6064	Remote Similarity	NPC116458
0.6064	Remote Similarity	NPC246943
0.6042	Remote Similarity	NPC251417
0.5895	Remote Similarity	NPC605784
0.5816	Remote Similarity	NPC480466
0.5714	Remote Similarity	NPC480463
0.5699	Remote Similarity	NPC64305
0.5684	Remote Similarity	NPC611303
0.5638	Remote Similarity	NPC46420
0.5625	Remote Similarity	NPC148710
0.5532	Remote Similarity	NPC297987
0.5474	Remote Similarity	NPC271692
0.5426	Remote Similarity	NPC249281
0.5417	Remote Similarity	NPC59534
0.5368	Remote Similarity	NPC95090
0.5368	Remote Similarity	NPC27408
0.5368	Remote Similarity	NPC158674
0.5368	Remote Similarity	NPC136042
0.5333	Remote Similarity	NPC124155
0.5333	Remote Similarity	NPC35119
0.5312	Remote Similarity	NPC84362
0.5312	Remote Similarity	NPC349108
0.5306	Remote Similarity	NPC120099
0.5268	Remote Similarity	NPC277532
0.5243	Remote Similarity	NPC183672
0.5204	Remote Similarity	NPC219904
0.5189	Remote Similarity	NPC32641
0.5189	Remote Similarity	NPC256188
0.5155	Remote Similarity	NPC24043
0.5155	Remote Similarity	NPC488080
0.5155	Remote Similarity	NPC169977
0.5149	Remote Similarity	NPC265115
0.5143	Remote Similarity	NPC64425
0.5104	Remote Similarity	NPC77672
0.5104	Remote Similarity	NPC133671
0.5104	Remote Similarity	NPC135391
0.5104	Remote Similarity	NPC78263
0.5104	Remote Similarity	NPC250069
0.5088	Remote Similarity	NPC470716
0.5052	Remote Similarity	NPC8573
0.5051	Remote Similarity	NPC168584
0.5051	Remote Similarity	NPC60735
0.5051	Remote Similarity	NPC26230
0.5051	Remote Similarity	NPC488071
0.505	Remote Similarity	NPC276377
0.505	Remote Similarity	NPC355481
0.5047	Remote Similarity	NPC606657
0.5044	Remote Similarity	NPC470715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3434
0.1-0.2	5611
0.2-0.3	91
0.3-0.4	9
0.4-0.5	4
0.5-0.6	0
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7804	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