NPASS Compound

Natural Product: NPC324004

Natural Product ID	NPC324004
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	12-Hydroxyoctadecanoic Acid
IUPAC Name	12-hydroxyoctadecanoic acid
Synonyms	12-Hydroxy-Octadecanoic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL292352
PubChem CID	7789
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

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 57 56 0 0 0 0 0 0 0 0999 V2000 6.0172 1.8143 0.3417 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6580 1.2039 0.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8491 2.2175 -0.7264 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4964 1.8106 -1.1302 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2393 0.7221 -2.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5814 -0.6757 -1.8719 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0375 -1.4774 -0.7582 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3199 -1.0982 0.6337 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6318 -2.1200 1.5581 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1370 -2.1441 1.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4982 -0.8216 1.6414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9917 -0.8466 1.4618 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4436 -1.2164 0.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9513 -1.2077 -0.0203 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5214 0.1361 0.2908 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0040 1.2391 -0.6256 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6676 2.5321 -0.1784 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1333 2.4577 -0.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6337 2.1508 -1.3909 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0025 2.7014 0.7858 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4933 -2.8185 -0.9104 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6682 1.5766 -0.5401 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4047 1.3847 1.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8877 2.9069 0.3682 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7534 0.2206 -0.4302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1654 1.0764 1.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4324 2.7085 -1.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7495 3.0875 0.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8421 1.8127 -0.1966 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0292 2.7549 -1.6485 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6854 1.0700 -3.0693 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1233 0.7724 -2.3353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1294 -1.2101 -2.8157 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6514 -0.9739 -2.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9178 -1.5919 -0.8790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9760 -0.1297 0.9898 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4062 -1.2733 0.8408 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0754 -3.0913 1.2619 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8858 -1.8309 2.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2403 -2.8364 2.1860 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2075 -2.5877 0.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0549 -0.0367 0.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3128 -0.5461 2.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3730 0.1886 1.6869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4185 -1.4902 2.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0751 -0.4698 -0.6540 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0761 -2.2254 -0.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3246 -1.9056 0.7682 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2423 -1.5788 -1.0291 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3414 0.4052 1.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6288 0.0846 0.0645 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1628 1.0367 -1.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9291 1.3563 -0.4083 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2571 3.3343 -0.8120 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3348 2.7110 0.8679 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8097 2.0670 0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3922 -2.8334 -0.4798 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 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 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 7 21 1 0 1 22 1 0 1 23 1 0 1 24 1 0 2 25 1 0 2 26 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 8 36 1 0 8 37 1 0 9 38 1 0 9 39 1 0 10 40 1 0 10 41 1 0 11 42 1 0 11 43 1 0 12 44 1 0 12 45 1 0 13 46 1 0 13 47 1 0 14 48 1 0 14 49 1 0 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 17 54 1 0 17 55 1 0 20 56 1 0 21 57 1 0 M END

Standard InCHIKey	ULQISTXYYBZJSJ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H36O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)
SMILES	CCCCCCC(CCCCCCCCCCC(=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
NPO4268	Bacillus cereus	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8071129]
NPO4268	Bacillus cereus	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO4268	Bacillus cereus	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4268	Bacillus cereus	Species	Bacillaceae	Bacteria	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
Potency	51
EC50	1

Activity Type	# Activity
Individual protein	7
Others	45

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	21875.1	nM	PubChem BioAssay data set
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	21939.3	nM	PubChem BioAssay data set
NPT866	Individual protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT4003	Individual protein	G-protein coupled receptor 120	Homo sapiens	EC50	=	1737.8	nM	PMID[30108848]
NPT74	Individual protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	6165.2	nM	PubChem BioAssay data set
NPT74	Individual protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	5510.9	nM	PubChem BioAssay data set
NPT546	Individual protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Potency	n.a.	21939.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	19553.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	19496.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1949.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	154.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	13685.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	30899.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	21875.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	49116	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24544.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24616.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43409.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39014.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43646.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	6165.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	34669.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	4855.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10963.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	34481.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24410.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43774.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	27389.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12337.4	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 NPC324004 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	27964
0.1-0.2	19437
0.2-0.3	2046
0.3-0.4	235
0.4-0.5	94
0.5-0.6	47
0.6-0.7	14
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC328497
0.7143	Intermediate Similarity	NPC171736
0.7143	Intermediate Similarity	NPC301585
0.7143	Intermediate Similarity	NPC261080
0.7143	Intermediate Similarity	NPC132565
0.7143	Intermediate Similarity	NPC209970
0.7143	Intermediate Similarity	NPC216630
0.7143	Intermediate Similarity	NPC201844
0.7143	Intermediate Similarity	NPC301696
0.7143	Intermediate Similarity	NPC196924
0.7143	Intermediate Similarity	NPC307783
0.7143	Intermediate Similarity	NPC154186
0.7143	Intermediate Similarity	NPC149184
0.7143	Intermediate Similarity	NPC279026
0.7143	Intermediate Similarity	NPC113928
0.7143	Intermediate Similarity	NPC14227
0.7105	Intermediate Similarity	NPC243532
0.6944	Remote Similarity	NPC606120
0.6786	Remote Similarity	NPC155263
0.625	Remote Similarity	NPC200618
0.625	Remote Similarity	NPC255863
0.625	Remote Similarity	NPC99619
0.625	Remote Similarity	NPC131770
0.625	Remote Similarity	NPC136164
0.625	Remote Similarity	NPC90904
0.625	Remote Similarity	NPC245947
0.6222	Remote Similarity	NPC319007
0.6071	Remote Similarity	NPC214610
0.6071	Remote Similarity	NPC118968
0.6071	Remote Similarity	NPC183424
0.6071	Remote Similarity	NPC294085
0.5882	Remote Similarity	NPC424
0.5882	Remote Similarity	NPC36061
0.5882	Remote Similarity	NPC69510
0.5882	Remote Similarity	NPC77272
0.5882	Remote Similarity	NPC8219
0.5882	Remote Similarity	NPC290563
0.5882	Remote Similarity	NPC139029
0.5882	Remote Similarity	NPC281972
0.5882	Remote Similarity	NPC261831
0.5882	Remote Similarity	NPC87564
0.5862	Remote Similarity	NPC175342
0.5758	Remote Similarity	NPC604910
0.5714	Remote Similarity	NPC18712
0.5714	Remote Similarity	NPC74845
0.5714	Remote Similarity	NPC95145
0.5714	Remote Similarity	NPC268826
0.5714	Remote Similarity	NPC325642
0.5714	Remote Similarity	NPC65174
0.5588	Remote Similarity	NPC281245
0.5581	Remote Similarity	NPC470320
0.5556	Remote Similarity	NPC87394
0.5556	Remote Similarity	NPC602547
0.5455	Remote Similarity	NPC55023
0.5455	Remote Similarity	NPC21844
0.5429	Remote Similarity	NPC129972
0.5429	Remote Similarity	NPC301528
0.5429	Remote Similarity	NPC71317
0.5429	Remote Similarity	NPC92114
0.5429	Remote Similarity	NPC163746
0.5429	Remote Similarity	NPC103286
0.5405	Remote Similarity	NPC154245
0.5405	Remote Similarity	NPC85813
0.5405	Remote Similarity	NPC223697
0.5405	Remote Similarity	NPC6095
0.5357	Remote Similarity	NPC174368
0.5349	Remote Similarity	NPC325627
0.5312	Remote Similarity	NPC604140
0.5306	Remote Similarity	NPC227396
0.5227	Remote Similarity	NPC327112
0.5208	Remote Similarity	NPC88735
0.5172	Remote Similarity	NPC134782
0.5152	Remote Similarity	NPC317203
0.5143	Remote Similarity	NPC314679
0.5135	Remote Similarity	NPC321062
0.5128	Remote Similarity	NPC40082
0.5122	Remote Similarity	NPC304162
0.5111	Remote Similarity	NPC26500

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC324004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5996
0.1-0.2	2804
0.2-0.3	273
0.3-0.4	52
0.4-0.5	12
0.5-0.6	7
0.6-0.7	2
0.7-0.8	3
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
0.7143	Intermediate Similarity	NPD2270	Pre-clinical
0.7143	Intermediate Similarity	NPD633	Phase 3
0.7143	Intermediate Similarity	NPD9448	Phase 2
0.6071	Remote Similarity	NPD9655	Phase 4
0.6	Remote Similarity	NPD3198	Phase 2
0.5882	Remote Similarity	NPD3195	Phase 2
0.5882	Remote Similarity	NPD3196	Approved
0.5641	Remote Similarity	NPD3194	Phase 4
0.5588	Remote Similarity	NPD3729	Phase 4
0.5556	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5405	Remote Similarity	NPD4266	Phase 2
0.5227	Remote Similarity	NPD4246	Phase 2

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