NPASS Compound

Natural Product: NPC40082

Natural Product ID	NPC40082
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ostopanic Acid
IUPAC Name	(8E,10E)-7,12-dioxooctadeca-8,10-dienoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL478594
PubChem CID	6440816
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

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 50 49 0 0 0 0 0 0 0 0999 V2000 7.1868 2.3849 -0.8599 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3163 0.9549 -0.4617 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0175 0.3381 0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9520 0.3746 -1.0230 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6522 -0.2431 -0.5034 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8201 -1.6481 -0.1182 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7100 -2.4063 0.3811 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0831 -3.6549 0.6880 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3350 -2.2005 0.6379 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6729 -1.0876 0.4326 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7727 -1.0216 0.7530 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4551 0.0708 0.5575 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8562 0.2816 0.8220 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3915 1.3933 0.5765 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6826 -0.8021 1.3843 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4119 -1.5025 0.2777 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3092 -0.5426 -0.4497 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3271 0.0155 0.5085 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2249 0.9684 -0.2891 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4370 2.0693 -0.8843 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9395 1.8973 -2.0427 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2032 3.2759 -0.2673 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1214 2.9483 -0.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1864 2.4086 -1.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2986 2.8644 -0.4457 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0264 0.9055 0.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7775 0.3213 -1.2586 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2830 -0.7470 0.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6837 0.8526 0.9190 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2940 -0.2027 -1.9109 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7043 1.4036 -1.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9179 -0.1773 -1.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2837 0.3454 0.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6579 -1.7790 0.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1770 -2.1942 -1.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7058 -3.0383 1.0592 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1182 -0.2117 0.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2647 -1.8927 1.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8905 0.9231 0.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3810 -0.4194 2.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0218 -1.5246 1.9346 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9792 -2.3885 0.6398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7003 -1.8996 -0.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7164 0.2681 -0.9516 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9019 -1.0845 -1.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8680 0.5465 1.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9280 -0.8487 0.8795 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9540 1.3734 0.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7362 0.3555 -1.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6287 3.9766 -0.7475 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 7 8 2 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 1 23 1 0 1 24 1 0 1 25 1 0 2 26 1 0 2 27 1 0 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 6 34 1 0 6 35 1 0 9 36 1 0 10 37 1 0 11 38 1 0 12 39 1 0 15 40 1 0 15 41 1 0 16 42 1 0 16 43 1 0 17 44 1 0 17 45 1 0 18 46 1 0 18 47 1 0 19 48 1 0 19 49 1 0 22 50 1 0 M END

Standard InCHIKey	WTLVYAWQAPUBFY-UTLPMFLDSA-N
Standard InCHI	InChI=1S/C18H28O4/c1-2-3-4-6-11-16(19)13-9-10-14-17(20)12-7-5-8-15-18(21)22/h9-10,13-14H,2-8,11-12,15H2,1H3,(H,21,22)/b13-9+,14-10+
SMILES	CCCCCCC(=O)/C=C/C=C/C(=O)CCCCCC(=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
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3655798]
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6854337]
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20019	Ostodes paniculata	Species	Euphorbiaceae	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
ED50	1

Activity Type	# Activity
Cell line	1

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
NPT168	Cell line	P388	Mus musculus	ED50	=	1.5	ug ml-1	PMID[22647719]

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 NPC40082 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	30717
0.1-0.2	17485
0.2-0.3	1359
0.3-0.4	158
0.4-0.5	68
0.5-0.6	33
0.6-0.7	19
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8378	Intermediate Similarity	NPC251042
0.8378	Intermediate Similarity	NPC174447
0.8378	Intermediate Similarity	NPC122521
0.7838	Intermediate Similarity	NPC106851
0.7838	Intermediate Similarity	NPC282788
0.7838	Intermediate Similarity	NPC274927
0.7576	Intermediate Similarity	NPC18712
0.7576	Intermediate Similarity	NPC74845
0.7073	Intermediate Similarity	NPC325977
0.7073	Intermediate Similarity	NPC143396
0.6667	Remote Similarity	NPC235242
0.65	Remote Similarity	NPC477201
0.6452	Remote Similarity	NPC171736
0.6452	Remote Similarity	NPC301585
0.6452	Remote Similarity	NPC261080
0.6452	Remote Similarity	NPC132565
0.6452	Remote Similarity	NPC209970
0.6452	Remote Similarity	NPC216630
0.6452	Remote Similarity	NPC201844
0.6452	Remote Similarity	NPC301696
0.6452	Remote Similarity	NPC196924
0.6452	Remote Similarity	NPC307783
0.6452	Remote Similarity	NPC154186
0.6452	Remote Similarity	NPC149184
0.6452	Remote Similarity	NPC279026
0.6452	Remote Similarity	NPC113928
0.6452	Remote Similarity	NPC14227
0.6279	Remote Similarity	NPC329550
0.6129	Remote Similarity	NPC155263
0.5833	Remote Similarity	NPC424
0.5833	Remote Similarity	NPC36061
0.5833	Remote Similarity	NPC69510
0.5833	Remote Similarity	NPC77272
0.5833	Remote Similarity	NPC290563
0.5833	Remote Similarity	NPC139029
0.5833	Remote Similarity	NPC281972
0.5833	Remote Similarity	NPC261831
0.5833	Remote Similarity	NPC87564
0.5676	Remote Similarity	NPC95145
0.5676	Remote Similarity	NPC325642
0.5676	Remote Similarity	NPC65174
0.5556	Remote Similarity	NPC281245
0.5484	Remote Similarity	NPC214610
0.5484	Remote Similarity	NPC118968
0.5484	Remote Similarity	NPC183424
0.5484	Remote Similarity	NPC294085
0.5405	Remote Similarity	NPC8219
0.5405	Remote Similarity	NPC92114
0.5385	Remote Similarity	NPC154245
0.5385	Remote Similarity	NPC85813
0.5385	Remote Similarity	NPC223697
0.5385	Remote Similarity	NPC6095
0.5319	Remote Similarity	NPC322461
0.5312	Remote Similarity	NPC175342
0.5161	Remote Similarity	NPC268826
0.5128	Remote Similarity	NPC321062
0.5128	Remote Similarity	NPC87394
0.5128	Remote Similarity	NPC324004
0.5128	Remote Similarity	NPC328497
0.5128	Remote Similarity	NPC602547
0.5116	Remote Similarity	NPC482480
0.5116	Remote Similarity	NPC482481

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC40082 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5538
0.1-0.2	3304
0.2-0.3	260
0.3-0.4	30
0.4-0.5	9
0.5-0.6	5
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	Drug ID	Developmental Stage
0.6452	Remote Similarity	NPD2270	Pre-clinical
0.6452	Remote Similarity	NPD633	Phase 3
0.6452	Remote Similarity	NPD9448	Phase 2
0.5833	Remote Similarity	NPD3195	Phase 2
0.5833	Remote Similarity	NPD3196	Approved
0.5484	Remote Similarity	NPD9655	Phase 4
0.5385	Remote Similarity	NPD4266	Phase 2
0.5128	Remote Similarity	NPD3199	Clinical (unspecified phase)

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