NPASS Compound

Structure

NPC488581 OpenBabel06302215172D 42 46 0 0 1 0 0 0 0 0999 V2000 -0.7447 -0.1975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0462 -0.7197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5445 -1.0594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1408 -1.1493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2137 -2.1222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7171 -0.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1592 -0.5614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3795 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6897 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6897 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9383 1.5532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3620 1.3755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9199 0.9653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6996 0.4039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2759 0.5817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7977 0.6208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0925 1.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0219 0.7624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6302 1.5251 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5949 1.3797 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2031 2.1424 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8467 3.0506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8820 3.1960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5256 4.1041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5609 4.2495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2738 2.4332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4550 3.8133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1678 1.9970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9513 0.4716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3795 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6897 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6897 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5346 -0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5346 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 2.4389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 32 2 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 33 1 0 0 0 0 12 13 1 0 0 0 0 12 32 1 0 0 0 0 13 19 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 21 20 1 1 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 6 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 25 1 0 0 0 0 24 29 1 6 0 0 0 25 26 1 1 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 34 33 1 6 0 0 0 34 35 1 0 0 0 0 34 39 1 0 0 0 0 35 36 1 0 0 0 0 35 42 1 6 0 0 0 36 37 1 0 0 0 0 36 41 1 1 0 0 0 37 38 1 0 0 0 0 37 40 1 1 0 0 0 38 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.22
Volume:	569.045
LogP:	0.472
LogD:	0.561
LogS:	-3.732
# Rotatable Bonds:	5
TPSA:	195.6
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	6.292
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.225
MDCK Permeability:	1.716491169645451e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	91.05183410644531%
Volume Distribution (VD):	1.047
Pgp-substrate:	3.0054256916046143%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.476
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	0.993
Half-life (T1/2):	0.603

ADMET: Toxicity

hERG Blockers:	0.373
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.382
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.182
Skin Sensitization:	0.92
Carcinogencity:	0.574
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.035

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC488581

Natural Product ID:	NPC488581
*Common Name:**	IEMQJQZXAZDWFM-OSMZHOMFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IEMQJQZXAZDWFM-OSMZHOMFSA-N
Standard InCHI:	InChI=1S/C30H36O12/c31-13-23-25(35)26(36)28(38)30(42-23)41-22-9-6-15-3-1-2-4-17(32)8-5-16-7-10-21(19(12-16)18(22)11-15)40-29-27(37)24(34)20(33)14-39-29/h2,4,6-7,9-12,20,23-31,33-38H,1,3,5,8,13-14H2/b4-2+/t20-,23+,24-,25+,26-,27+,28+,29+,30+/m0/s1
SMILES:	C1/C=C/C(=O)CCc2ccc(c(-c3cc(C1)ccc3O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)c2)O[C@@H]1[C@@H]([C@H]([C@H](CO1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Shells; Leaves	n.a.	n.a.	PMID[18163585]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25420236]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26606246]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Green Leafy Covers	n.a.	n.a.	PMID[28520428]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12631	Corylus avellana	Species	Betulaceae	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	NP ID	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
Others	7

Activity Type	# Activity
Organism	5
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	18.1	%	PMID[28520428]
NPT621	Tissue	Plasma	Homo sapiens	Inhibition	=	12.6	%	PMID[28520428]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	10.0	mm	PMID[28520428]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	=	0.0	mm	PMID[28520428]
NPT314	Organism	Bacillus cereus	Bacillus cereus	IZ	=	5.0	mm	PMID[28520428]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	4.67	mm	PMID[28520428]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[28520428]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC488581 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	1352
0.2-0.3	2820
0.3-0.4	6720
0.4-0.5	10367
0.5-0.6	6514
0.6-0.7	7792
0.7-0.8	6176
0.8-0.85	550
0.85-0.9	35
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	817
0.2-0.3	1523
0.3-0.4	2584
0.4-0.5	2141
0.5-0.6	1129
0.6-0.7	500
0.7-0.8	131
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

Bioactivity similarity: Similar Natural Products in NPASS

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