NPASS Compound

Natural Product: NPC243959

Natural Product ID	NPC243959
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DFPMSGMNTNDNHN-VVEPWVCASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	3000627
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 73 77 0 0 0 0 0 0 0 0999 V2000 -0.8131 2.7579 -0.4708 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0905 2.0729 -0.0590 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2651 3.0253 -0.0615 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5014 2.2905 0.3640 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2959 0.8327 0.6205 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2466 0.1775 -0.1937 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4274 1.0332 -0.9221 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4026 -0.5963 0.6021 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4078 -1.9323 0.2397 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9488 -2.6894 1.4434 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1431 -4.1347 1.0536 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0358 -4.6175 0.1779 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6277 -5.0671 -1.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7295 -5.8161 -1.8918 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9373 -3.8437 0.0717 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0425 -2.5002 -0.0448 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5300 -2.1033 -1.2795 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5828 -1.3550 -1.5490 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8777 -1.0838 -2.8890 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9580 -0.3513 -3.2672 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8111 0.1549 -2.3054 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9889 0.9496 -2.6677 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0946 1.3154 -3.8589 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9663 1.2591 -1.5934 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1954 1.5652 -0.3509 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0129 2.0332 0.7757 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4490 2.1412 2.0217 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1877 2.5794 3.1209 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5278 2.9203 2.9783 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0720 2.8036 1.7188 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3295 2.3662 0.6258 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2497 3.3543 4.0788 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4239 0.4263 -0.0086 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5650 -0.0835 -0.9715 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4468 -0.8395 -0.6173 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2629 -0.0738 -4.6084 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2838 -4.8583 2.2370 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1409 -2.1244 1.8857 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5482 0.2061 0.4071 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4916 2.5257 -0.5858 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9371 4.0774 0.7984 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6485 2.7183 -1.5656 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0256 2.2023 -0.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8251 3.7670 -0.0564 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9471 1.7376 0.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3565 3.4610 -1.0797 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8515 2.7601 1.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0786 0.6606 1.6983 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7451 -0.4642 -0.9591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0976 -2.0953 -0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1613 -2.6302 2.2419 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1438 -4.2059 0.5343 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6844 -5.5852 0.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9706 -4.2050 -1.7477 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5206 -5.7063 -0.9837 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9203 -5.2575 -2.0975 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3806 -2.0561 0.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2287 -1.4672 -3.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5752 0.3511 -1.4143 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5596 2.1203 -1.9631 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4984 2.4148 -0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4015 1.8886 2.1926 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7421 2.6646 4.1010 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1295 3.0696 1.5972 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7812 2.2844 -0.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7602 2.7666 4.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2749 -1.0133 0.4367 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 -0.7780 -5.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2111 -4.7120 2.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0164 -1.6451 2.7593 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1234 0.3107 1.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0759 3.2657 -0.3081 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7272 4.5803 1.0950 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 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 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 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 25 33 1 0 33 34 1 0 34 35 2 0 20 36 1 0 11 37 1 0 10 38 1 0 5 39 1 0 4 40 1 0 3 41 1 0 7 2 1 0 16 9 1 0 35 18 1 0 34 21 1 0 31 26 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 1 3 46 1 6 4 47 1 1 5 48 1 1 6 49 1 6 9 50 1 6 10 51 1 1 11 52 1 6 12 53 1 1 13 54 1 0 13 55 1 0 14 56 1 0 16 57 1 1 19 58 1 0 24 59 1 0 24 60 1 0 25 61 1 6 27 62 1 0 28 63 1 0 30 64 1 0 31 65 1 0 32 66 1 0 35 67 1 0 36 68 1 0 37 69 1 0 38 70 1 0 39 71 1 0 40 72 1 0 41 73 1 0 M END

Standard InCHIKey	DFPMSGMNTNDNHN-VVEPWVCASA-N
Standard InCHI	InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1cc(c2C(=O)C[C@H](c3ccc(cc3)O)Oc2c1)O)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
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377852]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	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 NPC243959 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	14392
0.1-0.2	29437
0.2-0.3	5168
0.3-0.4	735
0.4-0.5	84
0.5-0.6	23
0.6-0.7	7
0.7-0.8	0
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC142860
1.0	High Similarity	NPC152538
1.0	High Similarity	NPC246469
1.0	High Similarity	NPC89088
0.8734	High Similarity	NPC291124
0.8734	High Similarity	NPC131157
0.8718	High Similarity	NPC97285
0.8171	Intermediate Similarity	NPC105095
0.8171	Intermediate Similarity	NPC177731
0.8171	Intermediate Similarity	NPC725
0.8	Intermediate Similarity	NPC105283
0.7179	Intermediate Similarity	NPC39351
0.6951	Remote Similarity	NPC479540
0.686	Remote Similarity	NPC271270
0.6344	Remote Similarity	NPC261254
0.622	Remote Similarity	NPC97052
0.619	Remote Similarity	NPC29830
0.6145	Remote Similarity	NPC219163
0.602	Remote Similarity	NPC241196
0.5978	Remote Similarity	NPC43587
0.5977	Remote Similarity	NPC236934
0.5895	Remote Similarity	NPC47140
0.5632	Remote Similarity	NPC138350
0.5632	Remote Similarity	NPC165482
0.5619	Remote Similarity	NPC469371
0.5591	Remote Similarity	NPC200708
0.5591	Remote Similarity	NPC604887
0.5579	Remote Similarity	NPC44328
0.5579	Remote Similarity	NPC79056
0.5521	Remote Similarity	NPC293629
0.5517	Remote Similarity	NPC206378
0.5443	Remote Similarity	NPC607702
0.5402	Remote Similarity	NPC26195
0.5385	Remote Similarity	NPC475246
0.5349	Remote Similarity	NPC169248
0.5349	Remote Similarity	NPC72649
0.5287	Remote Similarity	NPC170475
0.5263	Remote Similarity	NPC329203
0.5263	Remote Similarity	NPC222342
0.5111	Remote Similarity	NPC181014
0.5109	Remote Similarity	NPC127406
0.5056	Remote Similarity	NPC471457

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC243959 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4330
0.1-0.2	4694
0.2-0.3	117
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
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
0.5579	Remote Similarity	NPD7074	Phase 3

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