NPASS Compound

Structure

NPC72350 OpenBabel06302216032D 51 61 0 0 1 0 0 0 0 0999 V2000 -5.0395 1.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0395 2.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1734 3.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3074 2.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3074 1.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1734 1.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1734 0.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3074 -0.0302 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3074 -0.9698 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.1734 -1.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0395 -0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9055 -1.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7715 -0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7715 0.0302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9055 0.5302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0395 0.0302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1134 1.5083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1079 1.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5147 0.6993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 -1.4397 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6276 -1.9397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6428 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 0.9397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 0.4397 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8356 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1554 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3788 1.1031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7371 2.0366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9600 2.6660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 -2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1213 -3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1554 -3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 -2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1031 -4.3788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0366 -4.7371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6660 -3.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5643 3.6390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9710 4.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9655 4.4480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 51 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 4 49 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 27 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 11 16 2 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 14 19 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 1 0 0 0 0 18 19 1 0 0 0 0 20 28 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 39 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 29 30 1 0 0 0 0 29 39 1 0 0 0 0 30 35 2 0 0 0 0 30 31 1 0 0 0 0 31 32 2 0 0 0 0 32 33 1 0 0 0 0 33 38 1 0 0 0 0 33 34 2 0 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 39 40 1 0 0 0 0 40 45 2 0 0 0 0 40 41 1 0 0 0 0 41 42 2 0 0 0 0 42 43 1 0 0 0 0 43 48 1 0 0 0 0 43 44 2 0 0 0 0 44 45 1 0 0 0 0 44 46 1 0 0 0 0 46 47 1 0 0 0 0 47 48 1 0 0 0 0 49 50 1 0 0 0 0 50 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	262.14
Volume:	257.657
LogP:	0.518
LogD:	-0.299
LogS:	-0.59
# Rotatable Bonds:	6
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	3.84
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.1
MDCK Permeability:	0.00039601666503585875
Pgp-inhibitor:	0.001
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.76
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.405

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.291
Plasma Protein Binding (PPB):	30.336891174316406%
Volume Distribution (VD):	0.531
Pgp-substrate:	51.15849304199219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.419
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	2.322
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.288
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.513
Carcinogencity:	0.073
Eye Corrosion:	0.018
Eye Irritation:	0.868
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC72350

Natural Product ID:	NPC72350
*Common Name:**	GBMJYIMQYSSXMR-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GBMJYIMQYSSXMR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C40H36O11/c1-5-29-33(47-17-43-29)11-21(1)9-25-26(10-22-2-6-30-34(12-22)48-18-44-30)40-42-16-28-27(15-41-39(25)51-40)37(23-3-7-31-35(13-23)49-19-45-31)38(28)24-4-8-32-36(14-24)50-20-46-32/h1-8,11-14,25-28,37-40H,9-10,15-20H2
SMILES:	c1cc2c(cc1CC1C(Cc3ccc4c(c3)OCO4)C3OCC4C(COC1O3)C(c1ccc3c(c1)OCO3)C4c1ccc3c(c1)OCO3)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	102344899
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003419] Cyclobutane lignans

*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
NPO20995	Syringa pinnafolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20995	Syringa pinnafolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC72350 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	630
0.1-0.2	1883
0.2-0.3	5676
0.3-0.4	13454
0.4-0.5	6192
0.5-0.6	10752
0.6-0.7	3553
0.7-0.8	546
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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 NPC72350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	467
0.1-0.2	923
0.2-0.3	1946
0.3-0.4	3074
0.4-0.5	1685
0.5-0.6	909
0.6-0.7	142
0.7-0.8	4
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

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