NPASS Compound

Natural Product: NPC102822

Natural Product ID	NPC102822
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MOCOVNGOINOTNW-XXJDAYKBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3317744
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 54 59 0 0 0 0 0 0 0 0999 V2000 -1.9330 8.5442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6830 7.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1830 7.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9330 5.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4218 6.1290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1830 4.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6830 4.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9330 5.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 5.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3170 4.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8170 4.6471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5670 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0670 3.3481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8170 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3170 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9330 3.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6830 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1830 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9949 3.5163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6958 4.2663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6725 -0.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8170 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5565 0.5718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4330 5.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5926 4.1341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1830 9.8433 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 9.2942 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4911 8.1309 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9330 8.5442 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9225 3.1699 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1830 7.2452 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9765 6.4592 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3283 7.4425 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7724 5.0101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2265 1.5360 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1830 2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9330 0.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2577 5.6571 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8571 5.5099 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3426 0.2370 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3150 0.3880 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8302 -1.1491 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8216 -1.6914 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7197 0.8511 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7056 -0.3924 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4751 7.0251 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6383 7.2183 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9321 5.8940 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8506 4.9510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 18 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 22 26 1 0 15 27 1 1 14 28 1 0 7 29 1 6 6 30 1 0 8 2 1 0 16 10 1 0 23 25 1 1 17 7 1 0 23 15 1 0 16 21 1 6 1 31 1 0 1 32 1 0 1 33 1 0 3 34 1 0 6 35 1 1 8 36 1 1 9 37 1 0 9 38 1 0 10 39 1 6 14 40 1 1 17 41 1 1 19 42 1 0 21 43 1 0 21 44 1 0 22 45 1 6 24 46 1 0 24 47 1 0 26 48 1 0 27 49 1 0 28 50 1 0 29 51 1 0 29 52 1 0 29 53 1 0 30 54 1 0 M END

Standard InCHIKey	MOCOVNGOINOTNW-XXJDAYKBSA-N
Standard InCHI	InChI=1S/C20H24O10/c1-7-3-9(21)11(22)16(2)8(7)4-10-17-5-29-19(26,14(16)17)15(25)18(6-28-18)20(17,27)12(23)13(24)30-10/h3,8,10-12,14-15,22-23,25-27H,4-6H2,1-2H3/t8-,10+,11+,12-,14+,15+,16+,17+,18-,19-,20-/m0/s1
SMILES	CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@H]1OC(=O)[C@@H]([C@@]3([C@]41[C@@H]2[C@](O)(OC4)[C@@H]([C@]13CO1)O)O)O)C)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
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	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
Activity	10
IC50	6
CC50	10

Activity Type	# Activity
Cell line	18
Organism	4
Unchecked	4

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
NPT81	Cell line	A549	Homo sapiens	Activity	=	96.21	%	PMID[19715321]
NPT81	Cell line	A549	Homo sapiens	Activity	=	102.0	%	PMID[19761234]
NPT81	Cell line	A549	Homo sapiens	Activity	=	99.1	%	PMID[9134742]
NPT165	Cell line	HeLa	Homo sapiens	Activity	=	101.0	%	PMID[19124664]
NPT165	Cell line	HeLa	Homo sapiens	Activity	=	61.66	%	PubChem BioAssay data set
NPT180	Cell line	HCT-8	Homo sapiens	Activity	=	100.88	%	PMID[36399766]
NPT2311	Cell line	Calu-3	Homo sapiens	CC50	>	100000.0	nM	PMID[36399766]
NPT171	Cell line	MRC5	Homo sapiens	CC50	>	100000.0	nM	PMID[36399766]
NPT180	Cell line	HCT-8	Homo sapiens	CC50	>	100000.0	nM	PMID[36399766]
NPT65	Cell line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[36399766]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	=	9390.0	nM	PMID[36399766]
NPT28438	Unchecked	Unchecked	n.a.	Activity	=	61.73	%	PMID[36399766]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	=	3.98	ug.mL-1	PMID[36399766]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	5880.0	nM	PMID[36399766]
NPT30043	Cell line	Vero	Chlorocebus sabaeus	CC50	>	100000.0	nM	PMID[36399766]

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 NPC102822 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	17631
0.1-0.2	28795
0.2-0.3	3350
0.3-0.4	32
0.4-0.5	25
0.5-0.6	15
0.6-0.7	3
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
0.7188	Intermediate Similarity	NPC188667
0.7188	Intermediate Similarity	NPC204552
0.7188	Intermediate Similarity	NPC482434
0.7188	Intermediate Similarity	NPC610747
0.7077	Intermediate Similarity	NPC112038
0.6324	Remote Similarity	NPC97908
0.6232	Remote Similarity	NPC287343
0.6232	Remote Similarity	NPC474654
0.5714	Remote Similarity	NPC11252
0.5714	Remote Similarity	NPC289312
0.5694	Remote Similarity	NPC482435
0.5652	Remote Similarity	NPC604470
0.5507	Remote Similarity	NPC201992
0.5429	Remote Similarity	NPC51978
0.5417	Remote Similarity	NPC485622
0.5417	Remote Similarity	NPC604056
0.5352	Remote Similarity	NPC469488
0.5263	Remote Similarity	NPC485625
0.5195	Remote Similarity	NPC235539
0.5072	Remote Similarity	NPC208998
0.5065	Remote Similarity	NPC18547
0.5065	Remote Similarity	NPC474906
0.5063	Remote Similarity	NPC297179

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC102822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6275
0.1-0.2	2786
0.2-0.3	89
0.3-0.4	0
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