NPASS Compound

Natural Product: NPC600185

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 90 95 0 0 0 0 0 0 0 0999 V2000 -11.0929 0.2853 3.2228 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6991 -0.5120 2.1411 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3578 -0.6730 1.7714 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9971 -1.4634 0.7024 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6674 -1.5987 0.3676 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6449 -0.9767 1.0525 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2303 -1.1666 0.6353 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9054 -0.1023 -0.3576 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5284 -0.1465 -0.8764 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6092 -1.1134 -0.6635 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3206 -1.0436 -1.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4471 -2.0730 -0.9458 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7237 -1.9926 -0.2577 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9775 -2.3099 -0.7087 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1283 -2.1956 0.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3840 -2.6200 -0.4789 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2914 -1.6878 -1.1643 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9553 -0.6201 -0.3835 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1788 -0.7640 0.9635 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8007 0.2114 1.6869 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0312 0.0799 3.0489 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6021 -1.1053 3.6840 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2188 1.3755 1.0454 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8489 2.3843 1.7388 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2917 3.5731 1.1567 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0083 1.5412 -0.3059 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3798 0.5433 -1.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2414 0.7538 -2.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4735 -0.3962 -3.1093 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4969 -0.9114 -2.1780 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8854 0.2254 -1.5128 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9598 -1.7555 1.3653 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7034 -1.4196 1.8620 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6044 -1.5348 1.0689 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6607 -1.1910 1.5866 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9811 0.0379 -1.9893 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3079 0.1202 -2.5501 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6407 1.2379 -3.3498 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9028 1.0253 -2.2130 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1466 0.9343 -1.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1886 1.9797 -1.8807 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0760 2.2055 -0.7066 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0493 1.1930 0.3013 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9178 1.4610 1.1731 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0114 -0.1861 2.1226 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3487 -0.0424 2.4692 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5814 1.2854 3.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1763 0.4981 3.1446 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8848 -0.1749 4.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7890 -1.9570 0.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3763 -2.2243 -0.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6177 -1.1389 1.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1594 -2.1845 0.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6347 -0.1441 -1.1947 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9027 -1.9617 -0.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0579 -2.6574 -1.7298 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1804 -3.4629 -1.2320 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0177 -3.2017 0.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0683 -2.1933 -1.7718 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8645 -1.7158 1.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9795 -1.9661 3.0972 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0297 -1.1439 4.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4923 -1.1028 3.6946 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8810 3.3248 0.2427 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4241 4.1859 0.8299 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9567 4.1467 1.8404 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3476 2.4697 -0.7935 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9081 1.7437 -2.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3182 0.6934 -2.8589 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0376 -0.1082 -4.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2042 -1.2188 -3.2900 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0490 0.2393 -0.4155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7872 0.2393 -1.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2254 1.2077 -1.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7792 -1.6455 2.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6084 -1.0592 2.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7381 -0.4518 2.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4834 2.1838 -2.8028 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0378 1.2719 -4.2501 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6668 1.0914 -3.7166 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6248 1.8695 -2.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7967 1.7348 -2.7715 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6822 2.9468 -2.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1504 2.3054 -1.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8644 3.1853 -0.1943 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2854 0.5544 1.2992 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2500 1.8015 2.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2624 2.2622 0.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2616 0.3176 2.6867 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6419 0.5871 3.3215 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 1 0 13 14 2 0 14 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 20 23 2 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 15 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 11 36 2 0 36 37 1 0 37 38 1 0 36 39 1 0 39 40 2 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 6 45 1 0 45 46 2 0 46 3 1 0 43 8 1 0 40 9 1 0 34 13 1 0 30 17 1 0 27 18 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 0 5 51 1 0 7 52 1 0 7 53 1 0 8 54 1 6 10 55 1 0 14 56 1 0 16 57 1 0 16 58 1 0 17 59 1 6 19 60 1 0 22 61 1 0 22 62 1 0 22 63 1 0 25 64 1 0 25 65 1 0 25 66 1 0 26 67 1 0 28 68 1 0 28 69 1 0 29 70 1 0 29 71 1 0 31 72 1 0 31 73 1 0 31 74 1 0 32 75 1 0 33 76 1 0 35 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 39 81 1 0 41 82 1 0 41 83 1 0 42 84 1 0 42 85 1 0 44 86 1 0 44 87 1 0 44 88 1 0 45 89 1 0 46 90 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 NPC600185 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	27297
0.1-0.2	20261
0.2-0.3	1948
0.3-0.4	194
0.4-0.5	59
0.5-0.6	45
0.6-0.7	28
0.7-0.8	0
0.8-0.85	5
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	NPC256012
1.0	High Similarity	NPC610965
0.8254	Intermediate Similarity	NPC317272
0.8254	Intermediate Similarity	NPC268503
0.8143	Intermediate Similarity	NPC601503
0.8	Intermediate Similarity	NPC600054
0.8	Intermediate Similarity	NPC601504
0.7681	Intermediate Similarity	NPC610959
0.7639	Intermediate Similarity	NPC223690
0.7639	Intermediate Similarity	NPC9532
0.7432	Intermediate Similarity	NPC290005
0.7429	Intermediate Similarity	NPC240841
0.7397	Intermediate Similarity	NPC185639
0.7397	Intermediate Similarity	NPC251735
0.7397	Intermediate Similarity	NPC49075
0.7397	Intermediate Similarity	NPC599951
0.7246	Intermediate Similarity	NPC480592
0.7237	Intermediate Similarity	NPC601489
0.7237	Intermediate Similarity	NPC604804
0.72	Intermediate Similarity	NPC181796
0.72	Intermediate Similarity	NPC54654
0.72	Intermediate Similarity	NPC7715
0.72	Intermediate Similarity	NPC328155
0.72	Intermediate Similarity	NPC222661
0.72	Intermediate Similarity	NPC285931
0.7143	Intermediate Similarity	NPC605743
0.7013	Intermediate Similarity	NPC212237
0.6949	Remote Similarity	NPC314682
0.6923	Remote Similarity	NPC24260
0.6923	Remote Similarity	NPC611658
0.6842	Remote Similarity	NPC274716
0.6842	Remote Similarity	NPC167116
0.6842	Remote Similarity	NPC609821
0.6774	Remote Similarity	NPC185838
0.6667	Remote Similarity	NPC247639
0.6667	Remote Similarity	NPC25084
0.6585	Remote Similarity	NPC206900
0.6575	Remote Similarity	NPC603603
0.6462	Remote Similarity	NPC135538
0.6462	Remote Similarity	NPC24233
0.629	Remote Similarity	NPC213206
0.629	Remote Similarity	NPC188163
0.629	Remote Similarity	NPC328750
0.6234	Remote Similarity	NPC608819
0.6163	Remote Similarity	NPC41122
0.6163	Remote Similarity	NPC318805
0.6154	Remote Similarity	NPC311973
0.6154	Remote Similarity	NPC239824
0.6104	Remote Similarity	NPC290582
0.6104	Remote Similarity	NPC217748
0.6104	Remote Similarity	NPC182052
0.6104	Remote Similarity	NPC271013
0.6104	Remote Similarity	NPC42663
0.6104	Remote Similarity	NPC15414
0.6026	Remote Similarity	NPC279228
0.5974	Remote Similarity	NPC480591
0.5949	Remote Similarity	NPC600872
0.5882	Remote Similarity	NPC480586
0.5875	Remote Similarity	NPC254441
0.5875	Remote Similarity	NPC116465
0.5867	Remote Similarity	NPC76682
0.5867	Remote Similarity	NPC10908
0.5867	Remote Similarity	NPC63646
0.5867	Remote Similarity	NPC317145
0.5867	Remote Similarity	NPC198498
0.5867	Remote Similarity	NPC115284
0.5843	Remote Similarity	NPC201508
0.5789	Remote Similarity	NPC276890
0.573	Remote Similarity	NPC60295
0.5714	Remote Similarity	NPC8836
0.5663	Remote Similarity	NPC16357
0.5663	Remote Similarity	NPC302245
0.5588	Remote Similarity	NPC191376
0.557	Remote Similarity	NPC603853
0.5556	Remote Similarity	NPC286119
0.5529	Remote Similarity	NPC275680
0.5529	Remote Similarity	NPC22115
0.5517	Remote Similarity	NPC480590
0.5507	Remote Similarity	NPC321505
0.5507	Remote Similarity	NPC179825
0.55	Remote Similarity	NPC73492
0.55	Remote Similarity	NPC299990
0.55	Remote Similarity	NPC480587
0.5467	Remote Similarity	NPC30779
0.5443	Remote Similarity	NPC12424
0.5443	Remote Similarity	NPC129518
0.5443	Remote Similarity	NPC251580
0.5441	Remote Similarity	NPC609731
0.5362	Remote Similarity	NPC147390
0.5362	Remote Similarity	NPC428
0.5326	Remote Similarity	NPC175890
0.5233	Remote Similarity	NPC139783
0.5233	Remote Similarity	NPC65312
0.5233	Remote Similarity	NPC611798
0.5208	Remote Similarity	NPC475654
0.5181	Remote Similarity	NPC475393
0.5125	Remote Similarity	NPC227060
0.5111	Remote Similarity	NPC82457
0.5059	Remote Similarity	NPC229373
0.5054	Remote Similarity	NPC191132

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC600185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4188
0.1-0.2	4706
0.2-0.3	235
0.3-0.4	12
0.4-0.5	3
0.5-0.6	3
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.629	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8053	Approved
0.6207	Remote Similarity	NPD8054	Phase 4
0.5867	Remote Similarity	NPD8099	Discontinued
0.557	Remote Similarity	NPD8156	Discontinued
0.55	Remote Similarity	NPD8095	Phase 1

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