NPASS Compound

Natural Product: NPC101793

Natural Product ID	NPC101793
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VSUQUSVBOASRIA-QHCPKHFHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	73355595
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

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 3.7584 1.9197 1.2966 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6946 0.7694 1.1711 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2363 -0.4542 1.0049 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7985 -0.7977 0.9288 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4901 -1.4403 -0.3763 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8543 -2.7525 -0.5829 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5497 -3.3090 -1.8055 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9070 -2.5912 -2.7888 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5316 -1.2558 -2.5906 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 -0.5111 -3.6441 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3830 -1.0793 -4.6375 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7674 0.9775 -3.4278 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5077 1.2752 -1.9842 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8636 0.9944 -1.5252 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8515 0.5955 -2.3916 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1414 0.3313 -1.9892 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5154 0.4596 -0.6464 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5284 0.8589 0.2252 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8791 1.0042 1.6351 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1052 0.7479 1.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1808 0.3219 1.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7379 -1.0517 1.5001 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3953 1.2587 1.1900 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8051 0.1948 -0.2488 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2394 1.1199 -0.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4753 0.6208 -1.1468 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8361 -0.7049 -1.3732 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5093 -3.4887 0.4149 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1619 1.0243 1.2366 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3742 2.2625 0.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3049 2.7966 1.7193 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9424 1.6971 2.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9378 -1.2753 0.9161 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4818 -1.4528 1.7835 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1620 0.1059 1.0073 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8312 -4.3366 -1.9765 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6539 -2.9973 -3.7584 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8148 1.3594 -3.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0357 1.4596 -4.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7158 2.3723 -1.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5766 0.4855 -3.4479 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8915 0.0210 -2.6932 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1127 1.3180 2.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3732 0.8564 3.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9376 -1.8228 1.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1043 -1.0431 2.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5609 -1.3455 0.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1372 0.8682 0.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1378 2.2803 0.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8594 1.1844 2.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4527 1.4376 0.4971 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1919 -4.4029 0.7123 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6155 0.5378 0.3397 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6062 0.5064 2.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4065 2.0894 1.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 18 25 2 0 13 26 1 0 26 27 1 0 6 28 1 0 2 29 1 0 27 5 1 0 27 9 2 0 25 14 1 0 24 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 7 36 1 0 8 37 1 0 12 38 1 0 12 39 1 0 13 40 1 6 15 41 1 0 16 42 1 0 19 43 1 0 20 44 1 0 22 45 1 0 22 46 1 0 22 47 1 0 23 48 1 0 23 49 1 0 23 50 1 0 25 51 1 0 28 52 1 0 29 53 1 0 29 54 1 0 29 55 1 0 M END

Standard InCHIKey	VSUQUSVBOASRIA-QHCPKHFHSA-N
Standard InCHI	InChI=1S/C25H26O4/c1-15(2)5-7-18-20(26)9-8-19-21(27)14-23(28-24(18)19)16-6-10-22-17(13-16)11-12-25(3,4)29-22/h5-6,8-13,23,26H,7,14H2,1-4H3/t23-/m0/s1
SMILES	CC(=CCc1c(ccc2C(=O)C[C@@H](c3ccc4c(C=CC(C)(C)O4)c3)Oc12)O)C

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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s40502-015-0143-x]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1093/pcp/pcg054]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1134/S1021443709050069]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39683057]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	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
Inhibition	13
FC	2
IC50	3
GI	5

Activity Type	# Activity
Individual protein	7
Cell line	13
Others	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	50.0	%	PMID[24047800]
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	50.0	%	PMID[28522265]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.4	n.a.	PMID[28835349]
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	71.0	%	PMID[28140583]
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	5000.0	nM	PMID[28140583]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	1.4	n.a.	PMID[28140583]
NPT741	Individual protein	Tyrosinase	Homo sapiens	Inhibition	=	3.1	%	PMID[28140583]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	12930.0	nM	PMID[28522265]
NPT660	Cell line	SW480	Homo sapiens	IC50	=	9840.0	nM	PMID[28522265]
NPT83	Cell line	MCF7	Homo sapiens	GI	=	75.0	%	PMID[28522265]
NPT660	Cell line	SW480	Homo sapiens	GI	=	72.0	%	PMID[28522265]
NPT65	Cell line	HepG2	Homo sapiens	GI	=	14.0	%	PMID[28522265]
NPT2615	Cell line	HEK-293T	Homo sapiens	GI	=	25.0	%	PMID[28522265]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	24.0	%	PMID[28522265]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	0.0	%	PMID[28140583]
NPT65	Cell line	HepG2	Homo sapiens	Inhibition	=	76.5	%	PMID[28140583]
NPT81	Cell line	A549	Homo sapiens	Inhibition	=	0.0	%	PMID[28140583]
NPT83	Cell line	MCF7	Homo sapiens	Inhibition	=	71.2	%	PMID[28140583]
NPT660	Cell line	SW480	Homo sapiens	Inhibition	=	34.8	%	PMID[28140583]
NPT21742	Cell line	L02	Homo sapiens	GI	=	2.0	%	PMID[28522265]
NPT2	Others	Unspecified	n.a.	Inhibition	=	20.0	%	PMID[28522265]
NPT2	Others	Unspecified	n.a.	Inhibition	=	15.0	%	PMID[28522265]
NPT2	Others	Unspecified	n.a.	Inhibition	=	44.7	%	PMID[28140583]

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 NPC101793 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	19777
0.1-0.2	26346
0.2-0.3	3108
0.3-0.4	467
0.4-0.5	113
0.5-0.6	35
0.6-0.7	8
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
0.8	Intermediate Similarity	NPC160821
0.7887	Intermediate Similarity	NPC132592
0.7286	Intermediate Similarity	NPC39752
0.7121	Intermediate Similarity	NPC150408
0.6716	Remote Similarity	NPC164980
0.662	Remote Similarity	NPC23728
0.6618	Remote Similarity	NPC236766
0.6618	Remote Similarity	NPC59522
0.6522	Remote Similarity	NPC149026
0.6154	Remote Similarity	NPC110303
0.6154	Remote Similarity	NPC601247
0.6104	Remote Similarity	NPC477958
0.5972	Remote Similarity	NPC197252
0.5915	Remote Similarity	NPC91560
0.5867	Remote Similarity	NPC312973
0.5789	Remote Similarity	NPC36275
0.5769	Remote Similarity	NPC477957
0.575	Remote Similarity	NPC609256
0.561	Remote Similarity	NPC283234
0.5541	Remote Similarity	NPC66515
0.5513	Remote Similarity	NPC246948
0.55	Remote Similarity	NPC479215
0.5443	Remote Similarity	NPC479211
0.5432	Remote Similarity	NPC479212
0.5405	Remote Similarity	NPC221432
0.5405	Remote Similarity	NPC257097
0.5405	Remote Similarity	NPC75049
0.5375	Remote Similarity	NPC479213
0.5366	Remote Similarity	NPC111786
0.5325	Remote Similarity	NPC161506
0.5309	Remote Similarity	NPC57313
0.5238	Remote Similarity	NPC218226
0.5195	Remote Similarity	NPC608140
0.5181	Remote Similarity	NPC54577
0.5181	Remote Similarity	NPC192686
0.5181	Remote Similarity	NPC284820
0.5132	Remote Similarity	NPC310130
0.5125	Remote Similarity	NPC142405
0.5122	Remote Similarity	NPC214774
0.5122	Remote Similarity	NPC267375
0.5122	Remote Similarity	NPC40033
0.5119	Remote Similarity	NPC119209
0.5068	Remote Similarity	NPC472409
0.5067	Remote Similarity	NPC107572
0.5067	Remote Similarity	NPC32739
0.5065	Remote Similarity	NPC76338
0.5065	Remote Similarity	NPC250242

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC101793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2952
0.1-0.2	6115
0.2-0.3	79
0.3-0.4	4
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