NPASS Compound

Structure

NPC104274 OpenBabel06302215102D 26 30 0 0 1 0 0 0 0 0999 V2000 -1.6275 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6275 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 2.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 3.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7615 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3857 2.8035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9735 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3857 1.1855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 4 3 1 1 0 0 0 4 5 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 6 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 6 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 18 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 19 20 1 6 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 22 26 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.2
Volume:	370.471
LogP:	4.797
LogD:	3.576
LogS:	-5.037
# Rotatable Bonds:	3
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	3.688
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.726
MDCK Permeability:	2.930539267254062e-05
Pgp-inhibitor:	0.716
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.182
30% Bioavailability (F30%):	0.774

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	96.29107666015625%
Volume Distribution (VD):	2.747
Pgp-substrate:	1.5347193479537964%

ADMET: Metabolism

CYP1A2-inhibitor:	0.725
CYP1A2-substrate:	0.752
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.375
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.595
CYP2D6-inhibitor:	0.895
CYP2D6-substrate:	0.848
CYP3A4-inhibitor:	0.978
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	15.931
Half-life (T1/2):	0.078

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.617
Rat Oral Acute Toxicity:	0.207
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.8
Carcinogencity:	0.549
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC104274

Natural Product ID:	NPC104274
*Common Name:**	QXSFPRUSCMGQOM-LNNXQNCSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QXSFPRUSCMGQOM-LNNXQNCSSA-N
Standard InCHI:	InChI=1S/C22H27NO3/c24-22(23-11-3-4-12-23)21-17-6-2-1-5-15(17)7-9-18(21)16-8-10-19-20(13-16)26-14-25-19/h7-10,13,15,17-18,21H,1-6,11-12,14H2/t15-,17+,18-,21-/m1/s1
SMILES:	C1CC[C@H]2[C@H](C1)C=C[C@H](c1ccc3c(c1)OCO3)[C@@H]2C(=O)N1CCCC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	51055151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26213786]
NPO14795	Vitis coignetiae	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18069	Streptomyces coelicoflavus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16048	Euphorbia serrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21786	Culcitium serratifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15734	Euchresta horsfeldii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17297	Caragana pygmaea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15893	Solandra guttata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17517	Artemisia arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15369	Tabernaemontana rupicola	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14795	Vitis coignetiae	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16447	Potato virus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2913	Tabebuia pentaphylla	Species	Bignoniaceae	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

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 NPC104274 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	276
0.1-0.2	1256
0.2-0.3	3522
0.3-0.4	11855
0.4-0.5	7209
0.5-0.6	13984
0.6-0.7	4033
0.7-0.8	525
0.8-0.85	23
0.85-0.9	11
0.9-0.95	3
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 NPC104274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	669
0.2-0.3	947
0.3-0.4	2284
0.4-0.5	2685
0.5-0.6	1669
0.6-0.7	636
0.7-0.8	73
0.8-0.85	6
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