NPASS Compound

Natural Product: NPC39290

Natural Product ID	NPC39290
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bathymodiolamide A
IUPAC Name	[(2S,3R,4S)-4-(dodecanoylamino)-2-[(6Z,9Z,12Z)-hexadeca-6,9,12-trienoyl]oxy-3,5-dihydroxypentyl] hexadecanoate
Synonyms	Bathymodiolamide A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1773151
PubChem CID	54585951
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

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 146145 0 0 0 0 0 0 0 0999 V2000 -24.9365 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -23.6375 -0.8433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -22.3385 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -21.0394 -2.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.7404 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.4413 -3.8433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.1423 -4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.8433 -5.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.5442 -6.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2452 -6.8433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9462 -7.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6471 -8.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3481 -7.5933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.0490 -8.3433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2579 -7.3475 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 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1.7942 -10.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0933 -11.5442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3923 -12.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6913 -13.0442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9904 -13.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2894 -14.5442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5885 -15.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8875 -16.0442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1865 -16.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4856 -17.5442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7846 -18.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.0836 -19.0442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.3827 -19.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 -10.3923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7990 -9.6423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5490 -10.9413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6471 -9.8433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -25.6865 -1.3923 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -24.1865 1.2058 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -26.2356 0.6567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -24.3875 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0 0 0 9.5490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2797 -2.0303 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7010 -3.3481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2990 -1.8481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0490 -3.1471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4510 -4.6471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0173 -7.8363 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2870 -9.9250 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0538 -7.9952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5538 -10.5933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2548 -11.3433 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2452 -8.7452 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5442 -9.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0442 -12.0933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3433 -12.8433 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8433 -10.2452 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1423 -10.9952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6423 -13.5933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9413 -14.3433 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4413 -11.7452 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0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7201 -10.6844 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2410 -9.2289 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0490 -10.9413 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9462 -10.5933 0.0000 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 2 3 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 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 0 16 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 15 54 1 0 14 55 1 0 55 56 1 0 12 57 1 0 1 58 1 0 1 59 1 0 1 60 1 0 2 61 1 0 2 62 1 0 3 63 1 0 3 64 1 0 4 65 1 0 4 66 1 0 5 67 1 0 5 68 1 0 6 69 1 0 6 70 1 0 7 71 1 0 7 72 1 0 8 73 1 0 8 74 1 0 9 75 1 0 9 76 1 0 10 77 1 0 10 78 1 0 11 79 1 0 11 80 1 0 14 81 1 1 15 82 1 1 16 83 1 6 20 84 1 0 20 85 1 0 21 86 1 0 21 87 1 0 22 88 1 0 22 89 1 0 23 90 1 0 23 91 1 0 24 92 1 0 25 93 1 0 26 94 1 0 26 95 1 0 27 96 1 0 28 97 1 0 29 98 1 0 29 99 1 0 30100 1 0 31101 1 0 32102 1 0 32103 1 0 33104 1 0 33105 1 0 34106 1 0 34107 1 0 34108 1 0 35109 1 0 35110 1 0 39111 1 0 39112 1 0 40113 1 0 40114 1 0 41115 1 0 41116 1 0 42117 1 0 42118 1 0 43119 1 0 43120 1 0 44121 1 0 44122 1 0 45123 1 0 45124 1 0 46125 1 0 46126 1 0 47127 1 0 47128 1 0 48129 1 0 48130 1 0 49131 1 0 49132 1 0 50133 1 0 50134 1 0 51135 1 0 51136 1 0 52137 1 0 52138 1 0 53139 1 0 53140 1 0 53141 1 0 54142 1 0 55143 1 0 55144 1 0 56145 1 0 57146 1 0 M END

Standard InCHIKey	ZWRWCDYNQPJUJY-MWNPFMMGSA-N
Standard InCHI	InChI=1S/C49H89NO7/c1-4-7-10-13-16-19-21-23-25-28-31-34-37-40-47(53)56-43-45(57-48(54)41-38-35-32-29-26-24-22-20-17-14-11-8-5-2)49(55)44(42-51)50-46(52)39-36-33-30-27-18-15-12-9-6-3/h11,14,20,22,26,29,44-45,49,51,55H,4-10,12-13,15-19,21,23-25,27-28,30-43H2,1-3H3,(H,50,52)/b14-11-,22-20-,29-26-/t44-,45-,49+/m0/s1
SMILES	CCCCCCCCCCCC(=N[C@H]([C@H]([C@@H](OC(=O)CCCC/C=CC/C=CC/C=CCCC)COC(=O)CCCCCCCCCCCCCCC)O)CO)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	803.66	Volume:	912.769 ? Van der Waals volume.
Dense:	0.88	LogP:	13.412 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.839 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.03 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	44.0	Rigid Bonds:	6.0
TPSA:	125.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	0.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.018	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.534	Fsp³:	0.816
MCE-18:	6.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.704	Fluc inhibitor:	0.055 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.351	Promiscuous compounds:	0.653

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.072	MDCK Permeability:	-4.702
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
PAMPA:	0.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.739
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	99.207%	Volume Distribution (VD):	0.886
Fu:	0.616% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.023
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.487
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.04	CYP2C19-substrate:	0.972
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.441
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.064	CYP2C8-inhibitor:	1.0
HLM stability:	0.01 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

3.913

Half-life (T1/2):

2.461

ADMET: Toxicity

hERG Blockers:	0.799	hERG Blockers (10um):	0.731
Human Hepatotoxicity (H-HT):	0.384	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.179	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.998
Eye Irritation:	0.999	Respiratory Toxicity:	0.989
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.172
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.764
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.019
A549 Cytotoxicity:	0.971	Hek293 Cytotoxicity:	0.01
BCF:	-0.693 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.526 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.884 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.031 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO5885	Bathymodiolus thermophilus	Species	Mytilidae	Eukaryota	n.a.	gill	n.a.	PMID[21222464]
NPO5885	Bathymodiolus thermophilus	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5885	Bathymodiolus thermophilus	Species	Mytilidae	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
IC50	2

Activity Type	# Activity
Cell line	2

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	400.0	nM	PMID[21222464]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	100.0	nM	PMID[21222464]

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 NPC39290 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	18135
0.1-0.2	29371
0.2-0.3	2094
0.3-0.4	194
0.4-0.5	48
0.5-0.6	15
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9322	High Similarity	NPC159369
0.5902	Remote Similarity	NPC473559
0.5902	Remote Similarity	NPC324981
0.5429	Remote Similarity	NPC489083
0.541	Remote Similarity	NPC48218
0.541	Remote Similarity	NPC141481
0.541	Remote Similarity	NPC464342
0.5333	Remote Similarity	NPC330426
0.5333	Remote Similarity	NPC127091
0.5333	Remote Similarity	NPC22101
0.5246	Remote Similarity	NPC54925
0.5238	Remote Similarity	NPC103712
0.5161	Remote Similarity	NPC99959
0.5161	Remote Similarity	NPC291196
0.5161	Remote Similarity	NPC489236
0.5161	Remote Similarity	NPC489237

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC39290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5624
0.1-0.2	3375
0.2-0.3	131
0.3-0.4	17
0.4-0.5	3
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