NPASS Compound

Natural Product: NPC190851

Natural Product ID	NPC190851
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RHLFBPMNWQGUEI-MEPLLZJUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44258461
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 55 58 0 0 0 0 0 0 0 0999 V2000 8.4021 -2.8484 0.6537 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0202 -3.1841 0.7424 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1004 -2.1633 0.5050 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4681 -0.8861 0.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5217 0.0939 -0.0292 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1794 -0.1435 0.0358 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8086 -1.4591 0.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7464 -2.4324 0.5775 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1579 0.8619 -0.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5031 2.1490 -0.5060 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4779 3.0642 -0.7176 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7667 4.2501 -1.0018 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1660 2.6861 -0.6193 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8953 1.3748 -0.3053 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4417 0.9883 -0.2049 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4923 1.8582 -0.4056 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2089 3.1912 -0.7248 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1112 3.5598 -0.8208 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3883 4.8811 -1.1373 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2653 4.0600 -0.9252 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8224 1.5127 -0.3150 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3651 0.2587 -0.0130 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2428 0.4367 1.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2263 -0.6654 1.4000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9052 -0.9818 0.0920 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8254 -1.2894 -0.9142 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0221 -2.4755 -0.4688 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0668 -2.7853 -1.4508 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0809 -0.1566 -1.1272 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8113 -2.0315 0.2296 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2131 -0.1896 2.2901 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3800 0.4436 2.3188 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8687 0.5291 -0.1100 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6382 -2.4224 -0.3372 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9610 -3.7900 0.8043 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6948 -2.1370 1.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5032 -0.6242 0.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8799 1.1072 -0.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7402 -1.6454 0.4026 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4294 -3.4526 0.8226 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5501 2.4879 -0.5932 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6243 -0.0501 0.0436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2501 5.2839 -2.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3974 4.4032 -1.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5619 -0.4596 0.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7663 1.3999 1.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7968 -1.5678 1.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4065 -0.0471 -0.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3228 -1.5541 -1.8646 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7033 -3.3506 -0.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5115 -2.3316 0.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2639 -3.6054 -1.9325 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6315 -1.7958 -0.2756 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3362 0.7882 2.1083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5371 0.8562 2.0437 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 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 6 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 17 20 1 0 16 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 24 31 1 0 23 32 1 0 14 33 1 0 8 3 1 0 33 9 1 0 18 13 1 0 29 22 1 0 1 34 1 0 1 35 1 0 1 36 1 0 4 37 1 0 5 38 1 0 7 39 1 0 8 40 1 0 10 41 1 0 15 42 1 0 19 43 1 0 20 44 1 0 22 45 1 1 23 46 1 0 24 47 1 1 25 48 1 6 26 49 1 0 27 50 1 0 27 51 1 0 28 52 1 0 30 53 1 0 31 54 1 0 32 55 1 0 M END

Standard InCHIKey	RHLFBPMNWQGUEI-MEPLLZJUSA-N
Standard InCHI	InChI=1S/C22H22O11/c1-30-10-4-2-9(3-5-10)12-6-11(24)16-13(31-12)7-14(17(25)19(16)27)32-22-21(29)20(28)18(26)15(8-23)33-22/h2-7,15,18,20-23,25-29H,8H2,1H3/t15?,18-,20+,21?,22-/m1/s1
SMILES	COc1ccc(cc1)c1cc(=O)c2c(cc(c(c2O)O)O[C@H]2C([C@H]([C@@H](C(CO)O2)O)O)O)o1

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
NPO2621	Paederota lutea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2621	Paederota lutea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2621	Paederota lutea	Species	Plantaginaceae	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 NPC190851 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	20963
0.1-0.2	24721
0.2-0.3	2815
0.3-0.4	935
0.4-0.5	296
0.5-0.6	85
0.6-0.7	29
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8451	Intermediate Similarity	NPC45618
0.8333	Intermediate Similarity	NPC146792
0.7973	Intermediate Similarity	NPC58716
0.7838	Intermediate Similarity	NPC95090
0.7838	Intermediate Similarity	NPC27408
0.7733	Intermediate Similarity	NPC186807
0.7703	Intermediate Similarity	NPC58053
0.7	Intermediate Similarity	NPC22832
0.7	Intermediate Similarity	NPC605067
0.6795	Remote Similarity	NPC143851
0.679	Remote Similarity	NPC243930
0.6709	Remote Similarity	NPC93337
0.6707	Remote Similarity	NPC607707
0.6667	Remote Similarity	NPC609451
0.6628	Remote Similarity	NPC3583
0.6625	Remote Similarity	NPC105025
0.6618	Remote Similarity	NPC57030
0.6582	Remote Similarity	NPC39360
0.6582	Remote Similarity	NPC29763
0.6582	Remote Similarity	NPC210003
0.6506	Remote Similarity	NPC311830
0.642	Remote Similarity	NPC245014
0.642	Remote Similarity	NPC84265
0.642	Remote Similarity	NPC181712
0.642	Remote Similarity	NPC45638
0.6386	Remote Similarity	NPC601144
0.6375	Remote Similarity	NPC261866
0.6341	Remote Similarity	NPC201292
0.631	Remote Similarity	NPC602805
0.6296	Remote Similarity	NPC189142
0.6296	Remote Similarity	NPC77660
0.6265	Remote Similarity	NPC191306
0.6235	Remote Similarity	NPC469931
0.622	Remote Similarity	NPC610763
0.6118	Remote Similarity	NPC88023
0.6118	Remote Similarity	NPC309025
0.6023	Remote Similarity	NPC603300
0.6	Remote Similarity	NPC486578
0.5977	Remote Similarity	NPC211594
0.5952	Remote Similarity	NPC182045
0.5904	Remote Similarity	NPC168822
0.5851	Remote Similarity	NPC475382
0.5814	Remote Similarity	NPC80188
0.5814	Remote Similarity	NPC601710
0.5783	Remote Similarity	NPC289667
0.5765	Remote Similarity	NPC472459
0.5747	Remote Similarity	NPC220169
0.5714	Remote Similarity	NPC22062
0.5714	Remote Similarity	NPC473634
0.5714	Remote Similarity	NPC138811
0.5698	Remote Similarity	NPC237435
0.5698	Remote Similarity	NPC285197
0.5652	Remote Similarity	NPC204693
0.5647	Remote Similarity	NPC602537
0.5638	Remote Similarity	NPC124155
0.5632	Remote Similarity	NPC43211
0.5632	Remote Similarity	NPC284960
0.5632	Remote Similarity	NPC21666
0.5595	Remote Similarity	NPC110349
0.5595	Remote Similarity	NPC83283
0.5591	Remote Similarity	NPC46202
0.5581	Remote Similarity	NPC222936
0.5581	Remote Similarity	NPC27942
0.5556	Remote Similarity	NPC275722
0.5541	Remote Similarity	NPC212678
0.5529	Remote Similarity	NPC259152
0.5506	Remote Similarity	NPC601586
0.5484	Remote Similarity	NPC257566
0.5479	Remote Similarity	NPC198826
0.5476	Remote Similarity	NPC331652
0.5474	Remote Similarity	NPC473623
0.5474	Remote Similarity	NPC483707
0.5467	Remote Similarity	NPC283600
0.5465	Remote Similarity	NPC84362
0.5465	Remote Similarity	NPC73511
0.5455	Remote Similarity	NPC485299
0.5455	Remote Similarity	NPC609478
0.5417	Remote Similarity	NPC488089
0.5392	Remote Similarity	NPC311850
0.5385	Remote Similarity	NPC251417
0.5376	Remote Similarity	NPC607513
0.5361	Remote Similarity	NPC256760
0.5349	Remote Similarity	NPC64305
0.534	Remote Similarity	NPC488083
0.5294	Remote Similarity	NPC45165
0.5294	Remote Similarity	NPC135345
0.5287	Remote Similarity	NPC24043
0.5287	Remote Similarity	NPC603655
0.5281	Remote Similarity	NPC148710
0.5281	Remote Similarity	NPC120099
0.5281	Remote Similarity	NPC608742
0.5275	Remote Similarity	NPC172807
0.527	Remote Similarity	NPC145379
0.5238	Remote Similarity	NPC68592
0.5233	Remote Similarity	NPC19709
0.5227	Remote Similarity	NPC21100
0.5227	Remote Similarity	NPC117260
0.5217	Remote Similarity	NPC8856
0.52	Remote Similarity	NPC162313
0.5172	Remote Similarity	NPC297987
0.5172	Remote Similarity	NPC277205
0.5172	Remote Similarity	NPC37919
0.5172	Remote Similarity	NPC136042
0.5172	Remote Similarity	NPC323593
0.5172	Remote Similarity	NPC203500
0.5172	Remote Similarity	NPC234739
0.5169	Remote Similarity	NPC60735
0.5169	Remote Similarity	NPC26230
0.5169	Remote Similarity	NPC488071
0.5165	Remote Similarity	NPC488072
0.5155	Remote Similarity	NPC209296
0.5155	Remote Similarity	NPC150767
0.5135	Remote Similarity	NPC29353
0.5116	Remote Similarity	NPC473043
0.5111	Remote Similarity	NPC115760
0.5111	Remote Similarity	NPC229729
0.5109	Remote Similarity	NPC477848
0.5067	Remote Similarity	NPC184136
0.5055	Remote Similarity	NPC307518
0.5054	Remote Similarity	NPC254540
0.5054	Remote Similarity	NPC472607
0.5053	Remote Similarity	NPC65003
0.5051	Remote Similarity	NPC195257

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5148
0.1-0.2	3893
0.2-0.3	91
0.3-0.4	12
0.4-0.5	4
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
0.5698	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5155	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