NPASS Compound

Natural Product: NPC165483

Natural Product ID	NPC165483
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-(3,4-Dihydroxy-Phenyl)-3-[(2R,3R)-2-(3,4-Dihydroxy-Phenyl)-3,5,7-Trihydroxy-Chroman-8-Yl]-Propionic Acid Methyl Ester
IUPAC Name	methyl (3R)-3-(3,4-dihydroxyphenyl)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]propanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2304274
PubChem CID	11755072
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins

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 -3.5112 -1.1942 4.5457 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8039 -0.5517 3.3249 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8411 -0.4253 2.3454 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6988 -0.8915 2.5576 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0991 0.2393 1.0499 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8803 0.2365 0.1679 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1811 0.9126 -1.1106 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4245 0.9259 -1.6937 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6210 1.5829 -2.8994 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6027 2.2413 -3.5592 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3557 2.2251 -2.9692 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1541 1.5731 -1.7700 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3200 2.8834 -3.6210 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8233 2.8997 -4.7782 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3021 -1.1206 0.0056 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0441 -2.1949 -0.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4893 -3.4699 -0.5878 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1792 -3.6874 -0.2998 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5696 -2.6214 0.1411 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0026 -2.8649 0.4549 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7402 -1.5850 0.1301 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1814 -0.5042 1.0572 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0132 0.6944 0.9226 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9299 1.0314 1.8902 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7292 2.1557 1.7902 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5895 2.9606 0.6696 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6877 2.6527 -0.3089 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8926 1.5067 -0.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5743 3.4816 -1.4179 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3968 4.1023 0.5616 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8338 -0.2985 0.7481 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0298 -1.3662 0.2928 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3669 -1.2162 -1.1696 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3649 -4.9635 -0.4552 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 -2.0723 -0.7484 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0301 -0.6866 5.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4277 -1.1138 4.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8797 -2.2446 4.5532 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9798 -0.2621 0.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 1.3000 1.2116 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1137 0.8368 0.7463 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2841 0.4437 -1.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6135 1.5812 -3.3441 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1608 1.5850 -1.3421 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3794 3.3636 -3.0507 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3909 3.7550 -4.7165 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0924 -4.2963 -0.9354 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3975 -3.7393 -0.0685 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0969 -2.9951 1.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8312 -1.6940 0.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2515 -0.8741 2.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0392 0.4050 2.7630 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4566 2.4431 2.5353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1874 1.2770 -0.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0781 3.1693 -2.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3492 3.9962 0.2201 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9123 -1.6751 -1.8511 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1862 -5.0480 -1.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0116 -2.8042 -0.4717 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 3 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 10 14 1 0 6 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 26 30 1 0 22 31 1 0 31 32 1 0 21 33 1 0 18 34 1 0 16 35 1 0 12 7 1 0 32 15 1 0 32 19 2 0 28 23 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 0 5 40 1 0 6 41 1 1 8 42 1 0 9 43 1 0 12 44 1 0 13 45 1 0 14 46 1 0 17 47 1 0 20 48 1 0 20 49 1 0 21 50 1 6 22 51 1 1 24 52 1 0 25 53 1 0 28 54 1 0 29 55 1 0 30 56 1 0 33 57 1 0 34 58 1 0 35 59 1 0 M END

Standard InCHIKey	QNAHIWNQXWCADO-KTICBNGHSA-N
Standard InCHI	InChI=1S/C25H24O10/c1-34-22(33)9-13(11-2-4-15(26)18(29)6-11)23-20(31)10-17(28)14-8-21(32)24(35-25(14)23)12-3-5-16(27)19(30)7-12/h2-7,10,13,21,24,26-32H,8-9H2,1H3/t13-,21-,24-/m1/s1
SMILES	COC(=O)C[C@H](c1ccc(c(c1)O)O)c1c(cc(c2C[C@H]([C@@H](c3ccc(c(c3)O)O)Oc12)O)O)O

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
NPO32903	antirhea acutata	Species	Rubiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[11412982]

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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Others	2

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
NPT2	Others	Unspecified	n.a.	IC50	=	29100.0	nM	PMID[18955526]
NPT2	Others	Unspecified	n.a.	IC50	=	16300.0	nM	PMID[18955526]

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 NPC165483 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	10281
0.1-0.2	34564
0.2-0.3	4719
0.3-0.4	196
0.4-0.5	53
0.5-0.6	33
0.6-0.7	4
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
0.6494	Remote Similarity	NPC9309
0.6286	Remote Similarity	NPC184245
0.6286	Remote Similarity	NPC187801
0.6286	Remote Similarity	NPC610920
0.5972	Remote Similarity	NPC98083
0.5972	Remote Similarity	NPC608986
0.5789	Remote Similarity	NPC302549
0.5775	Remote Similarity	NPC58190
0.5775	Remote Similarity	NPC108811
0.5775	Remote Similarity	NPC170103
0.5775	Remote Similarity	NPC236202
0.5775	Remote Similarity	NPC262911
0.5775	Remote Similarity	NPC202742
0.5694	Remote Similarity	NPC246202
0.5694	Remote Similarity	NPC224161
0.5694	Remote Similarity	NPC46335
0.5694	Remote Similarity	NPC279406
0.5694	Remote Similarity	NPC486519
0.5541	Remote Similarity	NPC313116
0.5541	Remote Similarity	NPC603340
0.5395	Remote Similarity	NPC70409
0.5395	Remote Similarity	NPC204770
0.5395	Remote Similarity	NPC600551
0.5395	Remote Similarity	NPC601980
0.5395	Remote Similarity	NPC602065
0.5395	Remote Similarity	NPC611024
0.5385	Remote Similarity	NPC278548
0.5342	Remote Similarity	NPC277331
0.5342	Remote Similarity	NPC100482
0.5256	Remote Similarity	NPC600630
0.5256	Remote Similarity	NPC607896
0.5256	Remote Similarity	NPC611369
0.5122	Remote Similarity	NPC135021
0.5114	Remote Similarity	NPC479794
0.5062	Remote Similarity	NPC20050
0.5062	Remote Similarity	NPC223148
0.5057	Remote Similarity	NPC479793

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC165483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2947
0.1-0.2	6066
0.2-0.3	134
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