NPASS Compound

Natural Product: NPC532145

Natural Product ID	NPC532145
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,6-dihydroxy-2-phenyl-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,6-dihydroxy-2-phenyl-7-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 50 53 0 0 0 0 0 0 0 0999 V2000 -5.3054 -2.3196 1.4617 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7673 -0.9233 1.1285 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4327 -1.0988 0.8039 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8679 0.0971 0.2912 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5374 -0.1369 0.1192 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3967 0.4775 0.4843 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7894 -0.1447 0.0708 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0406 0.3517 0.3597 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1015 1.5188 1.0925 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 2.1398 1.5050 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9859 3.3140 2.2423 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3258 1.6425 1.2156 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4895 2.2795 1.6379 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3395 2.0379 1.3959 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4340 3.1000 2.0620 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4600 1.3475 0.9408 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3543 0.1843 0.2112 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5237 -0.5630 -0.2805 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3217 -1.7184 -1.0032 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3625 -2.4756 -1.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6617 -2.0508 -1.2559 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8750 -0.9010 -0.5369 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8086 -0.1494 -0.0444 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1397 -0.2441 -0.0355 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5270 0.2320 -1.0939 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8606 1.1614 -1.8704 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9602 0.6692 -0.8079 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6609 0.7455 -2.0206 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6056 -0.3833 0.0244 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9864 -1.4354 -0.8212 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7194 -2.8071 2.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3941 -2.2702 1.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2103 -2.9550 0.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9126 -0.3082 2.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2010 0.9675 0.8452 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7692 -1.0690 -0.5101 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5915 3.2687 3.1821 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6602 2.2410 2.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4384 1.7439 1.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3205 -2.0727 -1.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -3.3727 -2.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4811 -2.6313 -1.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8839 -0.5866 -0.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0326 0.7311 0.5051 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5538 -0.7649 -1.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5152 1.8674 -2.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9349 1.6750 -0.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6257 0.7391 -1.9068 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5353 0.0520 0.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8852 -1.2022 -1.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 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 9 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 17 24 1 0 4 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 2 1 0 12 6 1 0 23 18 1 0 24 8 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 1 4 35 1 1 7 36 1 0 11 37 1 0 13 38 1 0 16 39 1 0 19 40 1 0 20 41 1 0 21 42 1 0 22 43 1 0 23 44 1 0 25 45 1 6 26 46 1 0 27 47 1 1 28 48 1 0 29 49 1 1 30 50 1 0 M END

Standard InCHIKey	KIJPCEZNJSGANY-SICOIOHGSA-N
Standard InCHI	InChI=1S/C21H20O9/c1-9-16(23)19(26)20(27)21(28-9)30-14-8-13-15(18(25)17(14)24)11(22)7-12(29-13)10-5-3-2-4-6-10/h2-9,16,19-21,23-27H,1H3/t9-,16+,19+,20-,21+/m1/s1
SMILES	C[C@H]1O[C@@H](OC2=CC3=C(C(O)=C2O)C(=O)C=C(C2=CC=CC=C2)O3)[C@H](O)[C@@H](O)[C@H]1O

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
NPO16284	Scutellaria galericulata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16284	Scutellaria galericulata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16284	Scutellaria galericulata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16284	Scutellaria galericulata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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 NPC532145 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	20628
0.1-0.2	26015
0.2-0.3	2317
0.3-0.4	632
0.4-0.5	199
0.5-0.6	53
0.6-0.7	6
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8406	Intermediate Similarity	NPC45618
0.7297	Intermediate Similarity	NPC146792
0.6974	Remote Similarity	NPC58716
0.6795	Remote Similarity	NPC237435
0.6579	Remote Similarity	NPC331652
0.6364	Remote Similarity	NPC275722
0.6282	Remote Similarity	NPC19709
0.6154	Remote Similarity	NPC473043
0.5904	Remote Similarity	NPC43211
0.5795	Remote Similarity	NPC3583
0.5714	Remote Similarity	NPC115760
0.5542	Remote Similarity	NPC245014
0.5542	Remote Similarity	NPC84265
0.5506	Remote Similarity	NPC44931
0.5488	Remote Similarity	NPC58053
0.5488	Remote Similarity	NPC39360
0.5488	Remote Similarity	NPC29763
0.5488	Remote Similarity	NPC210003
0.5444	Remote Similarity	NPC22062
0.5444	Remote Similarity	NPC473634
0.5444	Remote Similarity	NPC138811
0.5422	Remote Similarity	NPC93337
0.5422	Remote Similarity	NPC95090
0.5422	Remote Similarity	NPC27408
0.5385	Remote Similarity	NPC204693
0.5357	Remote Similarity	NPC186807
0.5357	Remote Similarity	NPC181712
0.5357	Remote Similarity	NPC105025
0.5357	Remote Similarity	NPC472385
0.5352	Remote Similarity	NPC198826
0.5352	Remote Similarity	NPC57030
0.5349	Remote Similarity	NPC181616
0.5349	Remote Similarity	NPC601144
0.5349	Remote Similarity	NPC605067
0.5349	Remote Similarity	NPC606560
0.5341	Remote Similarity	NPC477848
0.5301	Remote Similarity	NPC261866
0.5294	Remote Similarity	NPC27942
0.5275	Remote Similarity	NPC210073
0.5238	Remote Similarity	NPC189142
0.5238	Remote Similarity	NPC77660
0.5213	Remote Similarity	NPC209296
0.5176	Remote Similarity	NPC45638
0.5172	Remote Similarity	NPC22832
0.5169	Remote Similarity	NPC172807
0.5169	Remote Similarity	NPC211594
0.5119	Remote Similarity	NPC249281
0.5119	Remote Similarity	NPC108831
0.5119	Remote Similarity	NPC238376
0.5119	Remote Similarity	NPC143851
0.5119	Remote Similarity	NPC182634
0.5116	Remote Similarity	NPC201292
0.5114	Remote Similarity	NPC311830
0.5114	Remote Similarity	NPC602805
0.5106	Remote Similarity	NPC470443
0.5068	Remote Similarity	NPC162313
0.5057	Remote Similarity	NPC191306
0.5057	Remote Similarity	NPC609451
0.5057	Remote Similarity	NPC611303
0.5056	Remote Similarity	NPC469931
0.5056	Remote Similarity	NPC190003

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC532145 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4719
0.1-0.2	4338
0.2-0.3	80
0.3-0.4	8
0.4-0.5	3
0.5-0.6	1
0.6-0.7	1
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
0.6795	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5213	Remote Similarity	NPD7054	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