NPASS Compound

Natural Product: NPC101191

Natural Product ID	NPC101191
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YFWMSXQNCPRTKO-ZUGPOPFOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3397954
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003541] Flavonoid-8-O-glucuronides

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 -3.7580 4.0361 0.6606 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6463 3.5503 0.0251 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3266 2.2205 0.0591 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1368 1.3488 0.7454 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2469 1.7946 1.3871 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5580 3.1507 1.3428 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7488 -0.0516 0.7477 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5241 -0.9640 1.4187 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1711 -2.3212 1.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8828 -3.1650 2.0531 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0285 -2.6696 0.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6435 -3.9985 0.7466 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4967 -4.3308 0.0602 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2547 -3.3752 -0.6032 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1249 -2.0631 -0.5948 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2909 -1.7088 0.1000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6489 -0.4515 0.1042 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6186 -1.0918 -1.2556 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6588 -0.3490 -0.7121 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9365 -0.3410 -1.4924 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0428 0.0645 -0.5152 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4823 1.0902 0.4057 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2598 1.7925 -0.0724 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6742 2.8921 -0.9819 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5798 3.6613 -0.5570 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1509 3.1223 -2.2232 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2758 0.9917 -0.5883 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2331 0.6082 1.6942 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1839 0.4833 -1.1870 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2452 -1.5017 -2.1460 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4077 -3.8162 -1.2740 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4053 -4.9462 1.4152 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0291 5.0965 0.6440 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0132 4.2660 -0.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4300 1.8968 -0.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9252 1.1398 1.9480 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4529 3.4846 1.8647 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4344 -0.7320 1.9693 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1786 -5.3574 0.0399 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8524 -0.6959 0.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8908 0.4754 -2.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3208 -0.8300 0.0922 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2799 1.8791 0.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8111 2.3098 0.8270 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2567 4.0676 -2.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1880 1.4040 2.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5291 -0.2928 -1.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9201 -1.5011 -3.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -4.3506 -2.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1803 -5.9220 1.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 4 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 23 27 1 0 22 28 1 0 21 29 1 0 20 30 1 0 14 31 1 0 12 32 1 0 6 1 1 0 17 7 1 0 27 19 1 0 16 11 1 0 1 33 1 0 2 34 1 0 3 35 1 0 5 36 1 0 6 37 1 0 8 38 1 0 13 39 1 0 19 40 1 1 20 41 1 6 21 42 1 1 22 43 1 1 23 44 1 1 26 45 1 0 28 46 1 0 29 47 1 0 30 48 1 0 31 49 1 0 32 50 1 0 M END

Standard InCHIKey	YFWMSXQNCPRTKO-ZUGPOPFOSA-N
Standard InCHI	InChI=1S/C21H18O11/c22-9-6-11(24)17(31-21-16(27)14(25)15(26)19(32-21)20(28)29)18-13(9)10(23)7-12(30-18)8-4-2-1-3-5-8/h1-7,14-16,19,21-22,24-27H,(H,28,29)/t14-,15-,16+,19-,21+/m0/s1
SMILES	c1ccc(cc1)c1cc(=O)c2c(cc(c(c2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)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
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	whole plant	n.a.	n.a.	PMID[25637363]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20278	Scutellaria indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20278	Scutellaria indica	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell line	1

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	30000.0	nM	PubChem BioAssay data set

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 NPC101191 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	23455
0.1-0.2	24289
0.2-0.3	1627
0.3-0.4	436
0.4-0.5	28
0.5-0.6	8
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC210094
0.8493	Intermediate Similarity	NPC135277
0.6875	Remote Similarity	NPC49344
0.6875	Remote Similarity	NPC237435
0.6548	Remote Similarity	NPC222674
0.6471	Remote Similarity	NPC107987
0.642	Remote Similarity	NPC472385
0.6386	Remote Similarity	NPC264735
0.6353	Remote Similarity	NPC600989
0.6265	Remote Similarity	NPC282169
0.619	Remote Similarity	NPC608742
0.6087	Remote Similarity	NPC131624
0.6071	Remote Similarity	NPC20505
0.6	Remote Similarity	NPC43211
0.5814	Remote Similarity	NPC115760
0.5581	Remote Similarity	NPC198324
0.5517	Remote Similarity	NPC235260
0.5517	Remote Similarity	NPC155763
0.5402	Remote Similarity	NPC138927
0.5135	Remote Similarity	NPC301323
0.5135	Remote Similarity	NPC600177
0.5067	Remote Similarity	NPC188203

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC101191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3877
0.1-0.2	5171
0.2-0.3	91
0.3-0.4	10
0.4-0.5	0
0.5-0.6	0
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
0.6875	Remote Similarity	NPD4338	Clinical (unspecified phase)

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