NPASS Compound

Structure

NPC203890 OpenBabel06302215582D 28 30 0 0 1 0 0 0 0 0999 V2000 2.7640 2.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2194 1.9215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2208 1.9738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6734 1.0305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6665 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0514 -0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9220 1.9464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 13 1 0 0 0 0 5 6 1 0 0 0 0 5 28 1 1 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 27 1 1 0 0 0 8 13 1 0 0 0 0 8 9 1 0 0 0 0 8 26 1 1 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 15 14 1 1 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.15
Volume:	368.338
LogP:	-1.817
LogD:	-1.779
LogS:	-1.888
# Rotatable Bonds:	5
TPSA:	186.37
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	5.099
Fsp3:	0.824
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.492
MDCK Permeability:	0.00010648511670297012
Pgp-inhibitor:	0.002
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.864
20% Bioavailability (F20%):	0.166
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	19.346050262451172%
Volume Distribution (VD):	0.298
Pgp-substrate:	61.777435302734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	1.328
Half-life (T1/2):	0.732

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.42
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.067
Carcinogencity:	0.844
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC203890

Natural Product ID:	NPC203890
*Common Name:**	JXRURJXEYMRHCO-XBDCZORHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JXRURJXEYMRHCO-XBDCZORHSA-N
Standard InCHI:	InChI=1S/C17H26O11/c1-7(19)4-16(24)5-9(20)17(25)2-3-26-15(13(16)17)28-14-12(23)11(22)10(21)8(6-18)27-14/h2-3,8-15,18,20-25H,4-6H2,1H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1
SMILES:	CC(=O)C[C@@]1(C[C@H]([C@@]2(C=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO1869	Schizanthus grahamii	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22047009]
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24262004]
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25951057]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO803	Adonis annua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21021	Hemisteptia lyrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO803	Adonis annua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3076	Cordyline australis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1869	Schizanthus grahamii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11307.1	Wigandia urens var. caracasana	Varieties	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21021	Hemisteptia lyrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO803	Adonis annua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9735	Campnosperma panamense	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1132	Aster mongolicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4937	Pedicularis artselaeri	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10859	Myoporum laetum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9288	Litsea dealbata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11352	Centaurea cyanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4647	Leptothyrsa sprucei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13557	Coniochaeta hoffmannii	Species	Coniochaetaceae	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 NPC203890 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	206
0.1-0.2	1591
0.2-0.3	5804
0.3-0.4	11393
0.4-0.5	12358
0.5-0.6	8232
0.6-0.7	2942
0.7-0.8	142
0.8-0.85	23
0.85-0.9	6
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 NPC203890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	2281
0.2-0.3	3999
0.3-0.4	1782
0.4-0.5	520
0.5-0.6	300
0.6-0.7	81
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

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