NPASS Compound

Natural Product: NPC608141

Natural Product ID	NPC608141
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JEUSOLAWSNFKCL-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2007584
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

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 56 57 0 0 0 0 0 0 0 0999 V2000 3.6463 -0.4195 2.1857 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3984 -0.1287 1.2244 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8585 0.0927 -0.1478 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3766 -0.0893 -0.1284 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8100 0.1279 -1.4962 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3131 -0.0409 -1.5482 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4201 0.9001 -0.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9519 0.7071 -0.7097 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5001 0.9125 -2.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9534 0.7885 -2.2755 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6232 -0.4995 -2.0951 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7600 -1.1701 -0.7986 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5330 -0.3594 0.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9218 -0.3925 0.0788 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6963 0.3040 0.9671 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0976 1.0293 1.9626 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7470 1.0775 2.0951 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9465 0.3707 1.1952 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8320 -0.0166 1.5120 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6897 -1.0847 1.4225 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1544 -2.3133 1.0416 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0364 -0.9391 1.7019 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5570 0.2817 2.0783 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6769 1.3429 2.1622 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3504 1.2167 1.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5049 2.3128 1.9891 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1780 1.1055 -0.4601 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3860 -0.6250 -0.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9476 0.6796 0.5409 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1655 -1.1228 0.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2590 -0.5898 -2.2188 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1021 1.1391 -1.8389 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0143 0.1913 -2.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0255 -1.0886 -1.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2703 1.9596 -0.9737 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1539 0.8418 0.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3598 1.5210 -0.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1902 -0.2317 -0.2219 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1482 1.9334 -2.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9621 0.2072 -2.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5179 1.6196 -1.7197 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1572 1.1368 -3.3594 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6713 -0.4835 -2.5829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1220 -1.2713 -2.8138 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4653 -2.0744 -0.9936 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8459 -1.5971 -0.3880 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3865 -0.9793 -0.7255 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7859 0.2866 0.8893 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7396 1.5670 2.6454 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2754 1.6547 2.8872 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8881 0.4087 1.3314 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2129 -2.5349 0.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7108 -1.7810 1.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6114 0.4128 2.3010 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0676 2.3140 2.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2053 2.7919 1.1475 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 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 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 2 19 1 0 19 20 2 0 20 21 1 0 20 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 18 13 1 0 25 19 1 0 3 27 1 0 3 28 1 0 4 29 1 0 4 30 1 0 5 31 1 0 5 32 1 0 6 33 1 0 6 34 1 0 7 35 1 0 7 36 1 0 8 37 1 0 8 38 1 0 9 39 1 0 9 40 1 0 10 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 14 47 1 0 15 48 1 0 16 49 1 0 17 50 1 0 18 51 1 0 21 52 1 0 22 53 1 0 23 54 1 0 24 55 1 0 26 56 1 0 M END

Standard InCHIKey	JEUSOLAWSNFKCL-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C23H30O3/c24-20(23-21(25)17-12-18-22(23)26)16-11-6-4-2-1-3-5-8-13-19-14-9-7-10-15-19/h7,9-10,12,14-15,17-18,25-26H,1-6,8,11,13,16H2
SMILES	O=C(CCCCCCCCCCc1ccccc1)c1c(O)cccc1O

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
NPO28881	Virola sebifera	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39065009]
NPO28881	Virola sebifera	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28881	Virola sebifera	Species	Myristicaceae	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
GI50	59

Activity Type	# Activity
Cell line	59

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
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	19998.62	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	20044.72	nM	PubChem BioAssay data set
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	29107.17	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	19408.86	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	21281.39	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	18113.4	nM	PubChem BioAssay data set
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	18578.04	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	32960.97	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	23823.19	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	21183.61	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	45708.82	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	23713.74	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	23496.33	nM	PubChem BioAssay data set
NPT577	Cell line	RXF 631	Homo sapiens	GI50	n.a.	30760.97	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	26485.0	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	18879.91	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	20844.91	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	23823.19	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	44771.33	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	21281.39	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	20749.14	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	17947.34	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	21183.61	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	20653.8	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	25118.86	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	21281.39	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	20844.91	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	29040.23	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	18407.72	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	19998.62	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	25176.77	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	22698.65	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	21379.62	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	29512.09	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	27227.01	nM	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	20230.19	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	25292.98	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	19408.86	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	18197.01	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	20230.19	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	26977.39	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	61659.5	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	21428.91	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	16143.59	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	31622.78	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	15848.93	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	34673.69	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	27669.42	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	19543.39	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	18663.8	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	21183.61	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	20230.19	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	28119.01	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	21086.28	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	17701.09	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	38994.2	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	20749.14	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	31188.9	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	20749.14	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 NPC608141 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	24692
0.1-0.2	21570
0.2-0.3	3269
0.3-0.4	267
0.4-0.5	39
0.5-0.6	14
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188814
0.8974	High Similarity	NPC195262
0.8333	Intermediate Similarity	NPC196976
0.7556	Intermediate Similarity	NPC244441
0.6596	Remote Similarity	NPC159623
0.6538	Remote Similarity	NPC88345
0.6341	Remote Similarity	NPC121259
0.5854	Remote Similarity	NPC600129
0.5577	Remote Similarity	NPC475008
0.5556	Remote Similarity	NPC186097
0.5556	Remote Similarity	NPC475009
0.5455	Remote Similarity	NPC76938
0.5455	Remote Similarity	NPC32714
0.5366	Remote Similarity	NPC276111
0.5217	Remote Similarity	NPC474839
0.5217	Remote Similarity	NPC608363
0.5192	Remote Similarity	NPC259942
0.5192	Remote Similarity	NPC92624
0.5111	Remote Similarity	NPC241891
0.5111	Remote Similarity	NPC134829
0.5106	Remote Similarity	NPC607946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC608141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3890
0.1-0.2	4787
0.2-0.3	456
0.3-0.4	16
0.4-0.5	1
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