NPASS Compound

Natural Product: NPC546174

Natural Product ID	NPC546174
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Heptadecyl 3-chloropropanoate
IUPAC Name	heptadecyl 3-chloropropanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 62 61 0 0 0 0 0 0 0 0999 V2000 -8.4691 1.6549 0.5908 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6201 0.4791 1.0234 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3254 -0.3646 -0.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4871 -1.5560 0.1326 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1518 -1.1475 0.7280 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3564 -0.2950 -0.2185 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0530 0.0835 0.4323 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1857 -1.0707 0.8072 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7972 -1.9300 -0.3637 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0298 -1.1570 -1.4104 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2532 -0.5755 -0.8398 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9159 0.1640 -1.9788 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2129 0.7905 -1.4804 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1746 -0.2142 -0.9738 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4454 0.4602 -0.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1264 1.1588 -1.5758 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3707 1.9343 -1.2612 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4399 1.2999 -0.6912 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6161 0.8214 0.5570 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7034 0.9581 1.4026 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8844 0.1165 0.9895 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7553 -0.2897 2.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5071 1.1782 3.4027 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -9.1655 1.3454 -0.1993 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8465 2.4909 0.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0194 2.0881 1.4610 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1466 -0.0927 1.8073 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6996 0.8944 1.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8240 0.2650 -0.9379 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3052 -0.7520 -0.5792 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2713 -2.1239 -0.7875 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0111 -2.1565 0.8939 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3361 -0.6074 1.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5669 -2.0845 0.9071 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2048 -0.8016 -1.1955 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8844 0.6593 -0.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5184 0.8485 -0.1731 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3357 0.5932 1.4010 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7128 -1.6894 1.5563 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2846 -0.6678 1.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1246 -2.7263 0.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6807 -2.4170 -0.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7273 -1.8319 -2.2366 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6786 -0.3785 -1.8209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8741 -1.4310 -0.5075 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0724 0.1423 -0.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0974 -0.4844 -2.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2943 1.0068 -2.3398 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6369 1.4409 -2.2598 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9739 1.4866 -0.6237 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4996 -0.8818 -1.8226 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7639 -0.8690 -0.1738 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0914 -0.3655 -0.0300 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1973 1.1761 0.3396 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4782 0.3247 -2.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4617 1.7540 -2.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6750 2.4102 -2.2476 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0890 2.8657 -0.6521 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7725 0.7106 0.7840 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9241 -0.8114 0.3818 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6351 -0.8770 2.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8775 -0.9526 2.5658 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 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 6 36 1 0 7 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 21 59 1 0 21 60 1 0 22 61 1 0 22 62 1 0 M END

Standard InCHIKey	UDESWCQJPWPMKY-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C20H39ClO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-23-20(22)17-18-21/h2-19H2,1H3
SMILES	CCCCCCCCCCCCCCCCCOC(=O)CCCl

Calculated Properties

Physi-Chem Properties

Molecular Weight:	346.26	Volume:	384.631 ? Van der Waals volume.
Dense:	0.9	LogP:	7.788 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.442 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.685 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	1.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.151	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.054	Fsp³:	0.95
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.485	Fluc inhibitor:	0.131 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.999	Promiscuous compounds:	0.218

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.053	MDCK Permeability:	-4.826
Pgp-inhibitor:	0.001	Pgp-substrate:	0.043
PAMPA:	0.001 ? 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):	0.72
20% Bioavailability (F20%):	0.916	30% Bioavailability (F30%):	0.947
50% Bioavailability (F50%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055	MRP1:	0.94
Plasma Protein Binding (PPB):	99.939%	Volume Distribution (VD):	1.338
Fu:	0.828% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.218
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.614
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.01	CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.013	CYP2D6-substrate:	0.643
CYP3A4-inhibitor:	0.57	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.778	CYP2C8-inhibitor:	1.0
HLM stability:	0.611 ? 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):

5.016

Half-life (T1/2):

0.8

ADMET: Toxicity

hERG Blockers:	0.323	hERG Blockers (10um):	0.798
Human Hepatotoxicity (H-HT):	0.666	Drug-induced Liver Injury (DILI):	0.087
AMES Toxicity:	0.218	Rat Oral Acute Toxicity:	0.53
Maximum Recommended Daily Dose:	0.656	Skin Sensitization:	0.913
Carcinogencity:	0.605	Eye Corrosion:	0.971
Eye Irritation:	0.989	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.109	Ototoxicity:	0.228
Hematotoxicity:	0.715	Drug-induced Nephrotoxicity:	0.157
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.803	Hek293 Cytotoxicity:	0.096
BCF:	0.7 ? 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:	4.719 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.336 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.493 ? 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
NPO28447	Amaranthus viridis	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28447	Amaranthus viridis	Species	Amaranthaceae	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

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

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 NPC546174 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	27450
0.1-0.2	20864
0.2-0.3	1364
0.3-0.4	137
0.4-0.5	19
0.5-0.6	10
0.6-0.7	15
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	Natural Product ID
0.6897	Remote Similarity	NPC80641
0.6786	Remote Similarity	NPC322892
0.6667	Remote Similarity	NPC149299
0.6552	Remote Similarity	NPC154396
0.6429	Remote Similarity	NPC86545
0.6429	Remote Similarity	NPC286498
0.6429	Remote Similarity	NPC223374
0.6429	Remote Similarity	NPC196442
0.6429	Remote Similarity	NPC301398
0.6429	Remote Similarity	NPC608162
0.6429	Remote Similarity	NPC609004
0.6333	Remote Similarity	NPC80396
0.6129	Remote Similarity	NPC223675
0.6129	Remote Similarity	NPC68577
0.6071	Remote Similarity	NPC40965
0.5806	Remote Similarity	NPC154642
0.5806	Remote Similarity	NPC603612
0.5667	Remote Similarity	NPC223249
0.5667	Remote Similarity	NPC12904
0.5484	Remote Similarity	NPC286695
0.5484	Remote Similarity	NPC155872
0.5172	Remote Similarity	NPC248233
0.5172	Remote Similarity	NPC166804
0.5161	Remote Similarity	NPC476550
0.5152	Remote Similarity	NPC14608

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC546174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6502
0.1-0.2	2468
0.2-0.3	162
0.3-0.4	14
0.4-0.5	1
0.5-0.6	2
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
0.5676	Remote Similarity	NPD630	Approved
0.5405	Remote Similarity	NPD631	Phase 4

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