NPASS Compound

Structure

NPC5903 OpenBabel06302216122D 23 26 0 0 1 0 0 0 0 0999 V2000 -5.1595 1.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1959 1.4547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3569 0.9701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3571 0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5182 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6786 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6784 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5178 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 1.4541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9695 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8398 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 2.4226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6793 2.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5182 2.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5179 1.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 0.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6786 -0.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 -0.4846 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8394 -1.4535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6784 -1.9380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3986 2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2788 2.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 8 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 10 9 1 1 0 0 0 10 11 1 0 0 0 0 10 19 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 15 2 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 19 6 1 1 0 0 0 20 21 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.12
Volume:	313.791
LogP:	3.384
LogD:	3.377
LogS:	-5.016
# Rotatable Bonds:	3
TPSA:	46.15
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.87
Synthetic Accessibility Score:	3.452
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.81
MDCK Permeability:	7.004704821156338e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	90.1852035522461%
Volume Distribution (VD):	0.839
Pgp-substrate:	7.133763313293457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.256
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.882
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.748
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.746
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.524

ADMET: Excretion

Clearance (CL):	8.855
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.253
Human Hepatotoxicity (H-HT):	0.279
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.878
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.247
Skin Sensitization:	0.295
Carcinogencity:	0.387
Eye Corrosion:	0.02
Eye Irritation:	0.713
Respiratory Toxicity:	0.466

Download Data

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

Natural Product: NPC5903

Natural Product ID:	NPC5903
*Common Name:**	KGZXHPWOBPVKDK-BZSNNMDCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KGZXHPWOBPVKDK-BZSNNMDCSA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-19-10-4-6-12-14(8-10)22-17-13-7-5-11(20-2)9-15(13)23-18(21-3)16(12)17/h4-9,16-18H,1-3H3/t16-,17-,18-/m0/s1
SMILES:	COc1ccc2c(c1)O[C@H]1c3ccc(cc3O[C@@H]([C@@H]21)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO22676	Polygonum salicifolium	Species	Polygonaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[10479312]
NPO22676	Polygonum salicifolium	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8618	Hypotrachyna cirrhata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28258	Zingiber amaricans	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22973	Graphis scripta	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21733	Lithocarpus hancei	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21984	Pinus muricata	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23466	Buccinum striatissimum	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29044	Gymnopus peronatus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22740	Phyllanthus sellowianus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10704	Canthium subcordatum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22981	Sloanea rhodantha	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22858	Merendera raddeana	Species	Colchicaceae	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 NPC5903 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	483
0.1-0.2	1682
0.2-0.3	4541
0.3-0.4	12430
0.4-0.5	5893
0.5-0.6	5430
0.6-0.7	8516
0.7-0.8	3274
0.8-0.85	339
0.85-0.9	102
0.9-0.95	7
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 NPC5903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	947
0.2-0.3	1675
0.3-0.4	2790
0.4-0.5	1742
0.5-0.6	1008
0.6-0.7	523
0.7-0.8	79
0.8-0.85	5
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