NPASS Compound

Natural Product: NPC601997

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 67 72 0 0 0 0 0 0 0 0999 V2000 -4.5442 2.6043 4.4813 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0918 1.6480 3.5798 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5782 1.9506 2.3404 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1379 0.9682 1.4711 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1970 -0.3555 1.8141 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7260 -1.4089 0.8815 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2538 -1.0788 -0.3901 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4535 -0.8685 -1.5031 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8863 -0.0663 -2.5379 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0803 0.1433 -3.6546 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5142 0.9562 -4.7078 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 -0.4765 -3.6799 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4238 -1.2822 -2.6330 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2193 -1.4843 -1.5394 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8580 -2.3256 -0.3717 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5268 -2.7737 -0.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8498 -4.1210 -0.4092 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1270 -5.0849 -0.4278 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1736 -4.5303 -0.4180 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1931 -3.6030 -0.4003 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5113 -4.0268 -0.4093 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8664 -2.2508 -0.3734 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5421 -1.8416 -0.3646 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2455 -0.4755 -0.3374 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2951 0.3429 0.2047 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9591 1.7745 0.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4280 2.3967 -0.9537 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1383 3.7652 -0.9260 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5967 4.3745 -2.0511 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3857 4.5151 0.2086 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0995 5.8790 0.2431 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9246 3.8838 1.3129 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1784 4.6344 2.4656 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2040 2.5281 1.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5007 0.0740 -0.6710 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1187 0.1516 -2.0158 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0097 -1.3025 -0.3547 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2147 -1.5129 0.8663 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7838 -2.2565 1.9638 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7084 -0.6834 3.0521 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1533 0.3088 3.9305 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9737 3.4699 4.1403 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5306 3.0070 2.0658 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7503 1.2827 0.5224 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1148 -2.4053 1.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8616 0.4302 -2.5266 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5385 1.0022 -4.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2101 -0.3167 -4.5551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5439 -1.7622 -2.6665 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 -3.1969 -0.3726 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7960 -5.2386 0.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4522 -5.5944 -0.4392 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9280 -4.5397 -1.1714 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5460 0.0049 1.2253 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2373 1.8046 -1.8372 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2705 4.8799 -2.6380 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7982 6.5236 -0.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0066 5.2136 2.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6299 2.0953 2.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2539 0.8462 -0.4146 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9310 0.1561 -2.5879 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4432 -1.2712 0.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7477 -1.6613 -1.1011 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7734 -0.4956 0.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3184 -1.6766 2.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7620 -1.7196 3.3380 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5561 0.0723 4.9020 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 10 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 17 19 1 0 19 20 2 0 20 21 1 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 28 30 2 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 2 0 25 35 1 0 35 36 1 0 35 37 1 0 15 38 1 0 38 39 1 0 5 40 1 0 40 41 2 0 41 2 1 0 38 6 1 0 14 8 1 0 23 16 1 0 34 26 1 0 37 22 1 0 1 42 1 0 3 43 1 0 4 44 1 0 6 45 1 1 9 46 1 0 11 47 1 0 12 48 1 0 13 49 1 0 15 50 1 6 18 51 1 0 19 52 1 0 21 53 1 0 25 54 1 1 27 55 1 0 29 56 1 0 31 57 1 0 33 58 1 0 34 59 1 0 35 60 1 6 36 61 1 0 37 62 1 0 37 63 1 0 38 64 1 6 39 65 1 0 40 66 1 0 41 67 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 NPC601997 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	25486
0.1-0.2	21880
0.2-0.3	2166
0.3-0.4	204
0.4-0.5	47
0.5-0.6	43
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	8
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC609211
1.0	High Similarity	NPC610665
0.9219	High Similarity	NPC600630
0.9219	High Similarity	NPC607896
0.9219	High Similarity	NPC611369
0.9016	High Similarity	NPC601999
0.8906	High Similarity	NPC70409
0.8906	High Similarity	NPC204770
0.8906	High Similarity	NPC600551
0.8906	High Similarity	NPC601980
0.8906	High Similarity	NPC602065
0.8906	High Similarity	NPC611024
0.8594	High Similarity	NPC313116
0.8594	High Similarity	NPC603340
0.7538	Intermediate Similarity	NPC96576
0.7059	Intermediate Similarity	NPC58190
0.7059	Intermediate Similarity	NPC108811
0.7059	Intermediate Similarity	NPC170103
0.7059	Intermediate Similarity	NPC236202
0.7059	Intermediate Similarity	NPC262911
0.7059	Intermediate Similarity	NPC202742
0.6957	Remote Similarity	NPC246202
0.6957	Remote Similarity	NPC224161
0.6957	Remote Similarity	NPC46335
0.6957	Remote Similarity	NPC279406
0.6957	Remote Similarity	NPC486519
0.6944	Remote Similarity	NPC211561
0.6533	Remote Similarity	NPC278548
0.6111	Remote Similarity	NPC82917
0.6111	Remote Similarity	NPC277331
0.6111	Remote Similarity	NPC100482
0.5844	Remote Similarity	NPC226809
0.5802	Remote Similarity	NPC135021
0.5647	Remote Similarity	NPC86630
0.56	Remote Similarity	NPC294558
0.56	Remote Similarity	NPC18185
0.56	Remote Similarity	NPC263940
0.5595	Remote Similarity	NPC147743
0.5595	Remote Similarity	NPC4809
0.5595	Remote Similarity	NPC73517
0.5581	Remote Similarity	NPC106601
0.5581	Remote Similarity	NPC151474
0.5538	Remote Similarity	NPC268266
0.5538	Remote Similarity	NPC42760
0.5538	Remote Similarity	NPC220825
0.5538	Remote Similarity	NPC207179
0.5538	Remote Similarity	NPC167571
0.5538	Remote Similarity	NPC268342
0.5538	Remote Similarity	NPC278552
0.5517	Remote Similarity	NPC212614
0.5517	Remote Similarity	NPC205613
0.55	Remote Similarity	NPC65333
0.55	Remote Similarity	NPC302549
0.5488	Remote Similarity	NPC306267
0.5412	Remote Similarity	NPC9309
0.5333	Remote Similarity	NPC159526
0.5325	Remote Similarity	NPC184245
0.5325	Remote Similarity	NPC187801
0.5325	Remote Similarity	NPC610920
0.5244	Remote Similarity	NPC44192
0.5211	Remote Similarity	NPC178054
0.519	Remote Similarity	NPC155564
0.5181	Remote Similarity	NPC20050
0.5147	Remote Similarity	NPC261619
0.5147	Remote Similarity	NPC61477
0.5147	Remote Similarity	NPC78770
0.5147	Remote Similarity	NPC219876
0.5147	Remote Similarity	NPC126029
0.5147	Remote Similarity	NPC15658
0.5122	Remote Similarity	NPC46283
0.5122	Remote Similarity	NPC469944
0.5122	Remote Similarity	NPC134911
0.5056	Remote Similarity	NPC78074
0.5054	Remote Similarity	NPC478617

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC601997 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5565
0.1-0.2	3548
0.2-0.3	27
0.3-0.4	8
0.4-0.5	0
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
0.5147	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5147	Remote Similarity	NPD1613	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