NPASS Compound

Natural Product: NPC605437

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 79 83 0 0 0 0 0 0 0 0999 V2000 7.9123 1.6143 -1.9392 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2510 0.5866 -1.0970 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8912 0.2233 0.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1262 -0.0182 -1.4382 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4600 -1.0466 -0.6007 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9542 -1.1309 -0.9281 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3074 -0.3766 0.1329 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9988 -0.5901 0.6757 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6818 -1.9464 1.2416 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1775 -2.0540 1.3566 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2084 -0.6322 1.1464 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1662 0.0139 2.4497 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 -0.3538 0.8723 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5946 -0.6159 1.7097 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0241 -0.3852 1.5544 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3703 -0.1832 0.1134 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8113 0.2414 -0.0498 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6466 -1.0011 0.3137 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2503 1.3034 0.9188 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1072 0.5338 -1.4410 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2896 0.5692 -1.7929 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1003 0.7989 -2.4983 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7412 0.3255 -2.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3861 0.6135 -0.6556 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5453 2.0986 -0.5670 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9502 0.2240 -0.4313 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9872 1.3231 -0.7336 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4314 1.1365 -0.3096 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7249 -0.2785 0.0013 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6140 -1.0647 -1.2220 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3138 -0.6224 1.2827 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1238 0.2741 2.3013 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5479 -0.6121 0.7084 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3185 2.4529 -1.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8159 1.1709 -2.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2413 2.0628 -2.6849 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3878 0.7940 1.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8521 -0.8567 0.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9581 0.5901 0.2262 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6768 0.2597 -2.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9756 -1.9951 -0.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7547 -2.2159 -0.9860 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8912 -0.7313 -1.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4391 0.7159 -0.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9865 0.2074 1.5099 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1889 -2.0548 2.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9940 -2.7037 0.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0454 -2.3954 2.3958 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2813 -2.7842 0.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4052 1.0907 2.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9485 -0.5477 3.0485 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7125 -0.1467 3.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3754 -1.0958 2.7086 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4380 0.3970 2.2219 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5776 -1.3203 1.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3367 -1.2265 -0.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1511 -1.9261 -0.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6777 -0.8853 -0.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7076 -1.0220 1.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0507 1.9574 0.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4123 1.9155 1.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7275 0.8649 1.8455 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1552 1.8590 -2.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4361 0.2038 -3.3940 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0048 0.8383 -2.7972 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6806 -0.7867 -2.2669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2820 2.5663 0.3681 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5597 2.4474 -0.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8862 2.5424 -1.3625 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8516 -0.6516 -1.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3414 2.2040 -0.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0819 1.7122 -1.7747 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 1.7754 0.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0770 1.4508 -1.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2852 -0.4524 -2.1239 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0780 -2.0320 -1.1606 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6251 -1.3713 -1.5703 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0996 -1.6526 1.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9565 -0.1930 3.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 7 31 1 0 31 32 1 0 31 33 1 0 33 5 1 0 29 8 1 0 29 11 1 0 26 13 1 0 24 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 5 41 1 1 6 42 1 0 6 43 1 0 7 44 1 6 8 45 1 1 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 6 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 19 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 25 67 1 0 25 68 1 0 25 69 1 0 26 70 1 6 27 71 1 0 27 72 1 0 28 73 1 0 28 74 1 0 30 75 1 0 30 76 1 0 30 77 1 0 31 78 1 1 32 79 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 NPC605437 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	21014
0.1-0.2	24263
0.2-0.3	4165
0.3-0.4	316
0.4-0.5	51
0.5-0.6	32
0.6-0.7	11
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	Natural Product ID
0.7231	Intermediate Similarity	NPC470047
0.7231	Intermediate Similarity	NPC470046
0.6912	Remote Similarity	NPC470050
0.6912	Remote Similarity	NPC470051
0.6429	Remote Similarity	NPC67831
0.6429	Remote Similarity	NPC174051
0.6286	Remote Similarity	NPC486521
0.6286	Remote Similarity	NPC262870
0.6087	Remote Similarity	NPC90652
0.6087	Remote Similarity	NPC155255
0.6087	Remote Similarity	NPC470417
0.6087	Remote Similarity	NPC260992
0.6029	Remote Similarity	NPC470223
0.597	Remote Similarity	NPC470078
0.5946	Remote Similarity	NPC273669
0.5946	Remote Similarity	NPC484802
0.5946	Remote Similarity	NPC118647
0.5921	Remote Similarity	NPC63023
0.5921	Remote Similarity	NPC121566
0.5921	Remote Similarity	NPC100955
0.5921	Remote Similarity	NPC95243
0.589	Remote Similarity	NPC479667
0.5857	Remote Similarity	NPC470052
0.5833	Remote Similarity	NPC471224
0.5769	Remote Similarity	NPC189282
0.5769	Remote Similarity	NPC237402
0.56	Remote Similarity	NPC293081
0.557	Remote Similarity	NPC484792
0.5467	Remote Similarity	NPC6190
0.5455	Remote Similarity	NPC73506
0.5417	Remote Similarity	NPC470049
0.5333	Remote Similarity	NPC472239
0.5333	Remote Similarity	NPC484798
0.5278	Remote Similarity	NPC82902
0.5278	Remote Similarity	NPC474218
0.5211	Remote Similarity	NPC247220
0.52	Remote Similarity	NPC28227
0.5132	Remote Similarity	NPC484789
0.5132	Remote Similarity	NPC484801
0.5132	Remote Similarity	NPC484786
0.5132	Remote Similarity	NPC484787
0.5132	Remote Similarity	NPC484788
0.5128	Remote Similarity	NPC474327
0.5067	Remote Similarity	NPC147066
0.5065	Remote Similarity	NPC154101

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605437 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7136
0.1-0.2	1902
0.2-0.3	111
0.3-0.4	1
0.4-0.5	0
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

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