NPASS Compound

Natural Product: NPC155612

Natural Product ID	NPC155612
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ADHNUPOJJCKWRT-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	154212
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 52 51 0 0 0 0 0 0 0 0999 V2000 -4.8746 -0.2701 -2.2279 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6733 -1.1166 -1.3099 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8970 -0.7192 0.0742 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9168 -0.5958 1.1258 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7591 0.2801 1.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6072 0.2135 0.3211 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5610 1.2629 0.7302 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0656 1.0482 2.1080 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4634 -0.3112 2.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7082 -0.5503 1.2941 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7642 0.4627 1.5992 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9851 0.2069 0.6911 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5701 0.3620 -0.7226 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6159 0.1767 -1.7071 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8484 -0.1155 -1.6391 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7736 -0.3969 -0.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0454 -0.6813 -0.7243 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7792 -0.7733 -1.9305 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0412 -1.0693 -1.8588 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3362 -0.5886 -3.2132 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7721 0.7758 -1.9273 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8850 -0.7171 -2.4213 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3559 -0.2226 -3.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7144 -1.2107 -1.7933 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3213 -2.1957 -1.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5413 0.2586 -0.0006 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7261 -1.4291 0.5133 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5986 -1.6834 1.4782 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5576 -0.3589 2.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3164 0.1602 2.2866 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0543 1.3856 1.2712 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7887 0.4713 -0.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1088 -0.7869 0.2706 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9949 2.2835 0.6526 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7139 1.2511 0.0061 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2841 1.8449 2.3438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8429 1.1814 2.8658 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2145 -1.0873 2.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0484 -0.3900 3.2711 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0400 -1.5936 1.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3369 -0.4900 0.2453 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1376 0.4145 2.6258 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4147 1.4790 1.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2657 -0.8345 0.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7629 0.9685 0.9547 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0348 1.3501 -0.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7284 -0.3802 -0.9819 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1989 0.3380 -2.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3472 -0.1692 -2.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4073 -0.3872 0.4635 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5877 -0.8680 0.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9275 -0.3378 -3.9839 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 2 3 15 16 1 0 16 17 2 3 17 18 1 0 18 19 2 0 18 20 1 0 1 21 1 0 1 22 1 0 1 23 1 0 2 24 1 0 2 25 1 0 3 26 1 0 3 27 1 0 4 28 1 0 4 29 1 0 5 30 1 0 5 31 1 0 6 32 1 0 6 33 1 0 7 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 15 49 1 0 16 50 1 0 17 51 1 0 20 52 1 0 M END

Standard InCHIKey	ADHNUPOJJCKWRT-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h14-17H,2-13H2,1H3,(H,19,20)
SMILES	CCCCCCCCCCCCCC=CC=CC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	280.24	Volume:	329.555 ? Van der Waals volume.
Dense:	0.85	LogP:	6.766 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.858 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.35 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	3.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.245	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.243	Fsp³:	0.722
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:	0.48	Fluc inhibitor:	0.634 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.066 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.995	Promiscuous compounds:	0.577

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04	MDCK Permeability:	-4.767
Pgp-inhibitor:	0.0	Pgp-substrate:	0.057
PAMPA:	0.086 ? 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):	0.832
20% Bioavailability (F20%):	0.879	30% Bioavailability (F30%):	0.944
50% Bioavailability (F50%):	0.791

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.977
Plasma Protein Binding (PPB):	97.841%	Volume Distribution (VD):	-0.005
Fu:	1.537% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.501
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.177
BSEP inhibitor:	0.262

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.488	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.949
CYP2B6-substrate:	0.844	CYP2C8-inhibitor:	0.623
HLM stability:	0.002 ? 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):

2.415

Half-life (T1/2):

1.19

ADMET: Toxicity

hERG Blockers:	0.232	hERG Blockers (10um):	0.429
Human Hepatotoxicity (H-HT):	0.379	Drug-induced Liver Injury (DILI):	0.117
AMES Toxicity:	0.115	Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.137	Skin Sensitization:	0.988
Carcinogencity:	0.142	Eye Corrosion:	0.995
Eye Irritation:	0.997	Respiratory Toxicity:	0.885
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.322
Hematotoxicity:	0.118	Drug-induced Nephrotoxicity:	0.271
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.025
A549 Cytotoxicity:	0.309	Hek293 Cytotoxicity:	0.06
BCF:	0.897 ? 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:	4.304 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.783 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.613 ? 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
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20554	Astragalus complanatus	Species	Fabaceae	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 NPC155612 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	37156
0.1-0.2	10921
0.2-0.3	1431
0.3-0.4	239
0.4-0.5	81
0.5-0.6	15
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
0.697	Remote Similarity	NPC324224
0.6389	Remote Similarity	NPC487562
0.6364	Remote Similarity	NPC95145
0.6364	Remote Similarity	NPC325642
0.6364	Remote Similarity	NPC65174
0.6061	Remote Similarity	NPC424
0.6061	Remote Similarity	NPC36061
0.6061	Remote Similarity	NPC69510
0.6061	Remote Similarity	NPC77272
0.6061	Remote Similarity	NPC290563
0.6061	Remote Similarity	NPC139029
0.6061	Remote Similarity	NPC281972
0.6061	Remote Similarity	NPC261831
0.6061	Remote Similarity	NPC87564
0.6	Remote Similarity	NPC202716
0.5897	Remote Similarity	NPC487570
0.5758	Remote Similarity	NPC281245
0.5588	Remote Similarity	NPC92114
0.5556	Remote Similarity	NPC154245
0.5556	Remote Similarity	NPC472808
0.5556	Remote Similarity	NPC85813
0.5556	Remote Similarity	NPC223697
0.5556	Remote Similarity	NPC6095
0.5517	Remote Similarity	NPC63598
0.5517	Remote Similarity	NPC610009
0.5333	Remote Similarity	NPC221250
0.5278	Remote Similarity	NPC321062
0.5135	Remote Similarity	NPC59051
0.5111	Remote Similarity	NPC487569
0.5111	Remote Similarity	NPC108043

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC155612 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6724
0.1-0.2	2218
0.2-0.3	175
0.3-0.4	18
0.4-0.5	11
0.5-0.6	2
0.6-0.7	2
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
0.6061	Remote Similarity	NPD3195	Phase 2
0.6061	Remote Similarity	NPD3196	Approved
0.5556	Remote Similarity	NPD4266	Phase 2
0.5385	Remote Similarity	NPD3194	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