NPASS Compound

Natural Product: NPC141134

Natural Product ID	NPC141134
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YUQZOUNRPZBQJK-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	76015
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

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 32 31 0 0 0 0 0 0 0 0999 V2000 -3.8322 2.8495 -1.1967 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9439 1.6507 -1.3473 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0875 0.2088 -1.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1421 -0.5337 -0.6332 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6985 -0.1998 -0.9120 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7526 -0.9416 -0.0271 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6934 -0.6067 -0.3069 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -1.3798 0.6118 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0550 -1.0781 0.3711 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4624 0.3371 0.5611 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2583 0.9087 1.9172 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9233 0.8715 2.2746 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 3.8727 -1.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1245 -0.0421 -1.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0335 -0.0805 -2.5758 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3413 -1.6137 -0.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3415 -0.1872 0.4194 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5133 -0.5007 -1.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5616 0.8885 -0.8037 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8557 -2.0471 -0.2271 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9921 -0.7081 1.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9294 -0.8595 -1.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8302 0.4869 -0.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4524 -2.4666 0.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2844 -1.2766 1.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7100 -1.7452 0.9663 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2900 -1.3435 -0.7002 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5540 0.4225 0.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9610 1.0274 -0.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5371 1.9948 1.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9227 0.4756 2.6931 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4575 1.6162 1.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 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 1 13 1 0 3 14 1 0 3 15 1 0 4 16 1 0 4 17 1 0 5 18 1 0 5 19 1 0 6 20 1 0 6 21 1 0 7 22 1 0 7 23 1 0 8 24 1 0 8 25 1 0 9 26 1 0 9 27 1 0 10 28 1 0 10 29 1 0 11 30 1 0 11 31 1 0 12 32 1 0 M END

Standard InCHIKey	YUQZOUNRPZBQJK-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C11H20O/c1-2-3-4-5-6-7-8-9-10-11-12/h1,12H,3-11H2
SMILES	C#CCCCCCCCCCO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	168.15	Volume:	202.33 ? Van der Waals volume.
Dense:	0.831	LogP:	2.917 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.146 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.862 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	1.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.436	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.209	Fsp³:	0.818
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:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.003	Fluc inhibitor:	0.0 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.997	Promiscuous compounds:	0.077

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.036	MDCK Permeability:	-4.762
Pgp-inhibitor:	0.002	Pgp-substrate:	0.003
PAMPA:	0.297 ? 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):	0.471
20% Bioavailability (F20%):	0.122	30% Bioavailability (F30%):	0.265
50% Bioavailability (F50%):	0.549

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.666	MRP1:	0.001
Plasma Protein Binding (PPB):	91.028%	Volume Distribution (VD):	0.162
Fu:	7.208% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.835
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.848
BSEP inhibitor:	0.174

ADMET: Metabolism

CYP1A2-inhibitor:	0.977	CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.017	CYP2C19-substrate:	0.962
CYP2C9-inhibitor:	0.028	CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.409	CYP2D6-substrate:	0.781
CYP3A4-inhibitor:	0.883	CYP3A4-substrate:	0.101
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.909
HLM stability:	0.767 ? 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):

6.997

Half-life (T1/2):

0.843

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.263
Human Hepatotoxicity (H-HT):	0.702	Drug-induced Liver Injury (DILI):	0.007
AMES Toxicity:	0.318	Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.16	Skin Sensitization:	0.993
Carcinogencity:	0.548	Eye Corrosion:	0.995
Eye Irritation:	0.997	Respiratory Toxicity:	0.983
Drug-induced Neurotoxicity:	0.082	Ototoxicity:	0.205
Hematotoxicity:	0.179	Drug-induced Nephrotoxicity:	0.871
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.002	Hek293 Cytotoxicity:	0.048
BCF:	2.077 ? 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:	3.967 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.201 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.607 ? 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
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	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 NPC141134 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	45406
0.1-0.2	4125
0.2-0.3	267
0.3-0.4	31
0.4-0.5	9
0.5-0.6	16
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	Natural Product ID
0.6875	Remote Similarity	NPC152759
0.6875	Remote Similarity	NPC12231
0.625	Remote Similarity	NPC213764
0.5789	Remote Similarity	NPC126915
0.5789	Remote Similarity	NPC205141
0.5789	Remote Similarity	NPC24506
0.5789	Remote Similarity	NPC225783
0.5789	Remote Similarity	NPC279895
0.5789	Remote Similarity	NPC185538
0.5789	Remote Similarity	NPC181516
0.5789	Remote Similarity	NPC163556
0.5789	Remote Similarity	NPC139131
0.5789	Remote Similarity	NPC236797
0.5789	Remote Similarity	NPC291158
0.5789	Remote Similarity	NPC272998
0.5789	Remote Similarity	NPC112242
0.5789	Remote Similarity	NPC185041
0.5789	Remote Similarity	NPC147096
0.5263	Remote Similarity	NPC275462

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8533
0.1-0.2	590
0.2-0.3	24
0.3-0.4	1
0.4-0.5	0
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
0.5789	Remote Similarity	NPD2272	Phase 4
0.5789	Remote Similarity	NPD5383	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