NPASS Compound

Structure

NPC490466 OpenBabel06302216222D 42 46 0 0 1 0 0 0 0 0999 V2000 1.7321 -1.0000 0.0000 O 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 3 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 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 3 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 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 -2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 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 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 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 41 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 5 28 1 0 0 0 0 6 7 1 0 0 0 0 7 18 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 16 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 27 1 0 0 0 0 19 20 2 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 25 26 1 0 0 0 0 25 27 2 0 0 0 0 28 29 1 0 0 0 0 28 39 1 0 0 0 0 29 30 1 0 0 0 0 30 37 1 0 0 0 0 30 31 1 0 0 0 0 31 32 1 0 0 0 0 32 33 1 0 0 0 0 33 34 1 0 0 0 0 33 35 1 0 0 0 0 35 36 1 0 0 0 0 35 37 1 0 0 0 0 37 38 1 0 0 0 0 39 40 1 0 0 0 0 39 41 1 0 0 0 0 41 42 1 0 0 0 0 M CHG 1 17 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	597.15
Volume:	536.34
LogP:	-0.911
LogD:	0.284
LogS:	-2.043
# Rotatable Bonds:	6
TPSA:	270.75
# H-Bond Aceptor:	16
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.115
Synthetic Accessibility Score:	5.011
Fsp3:	0.423
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.499
MDCK Permeability:	2.9470988010871224e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.956
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	82.74018096923828%
Volume Distribution (VD):	0.769
Pgp-substrate:	24.76311683654785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.358
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.617
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.242
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC490466

Natural Product ID:	NPC490466
*Common Name:**	Delphinidin 3-sambubioside
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TWYYVOVDSNRIJM-UHFFFAOYSA-O
Standard InCHI:	InChI=1S/C26H28O16/c27-6-17-20(35)21(36)24(42-25-22(37)19(34)14(32)7-38-25)26(41-17)40-16-5-10-11(29)3-9(28)4-15(10)39-23(16)8-1-12(30)18(33)13(31)2-8/h1-5,14,17,19-22,24-27,32,34-37H,6-7H2,(H4-,28,29,30,31,33)/p+1
SMILES:	OCC1OC(OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC(O)=C(O)C(O)=C2)C(OC2OCC(O)C(O)C2O)C(O)C1O
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:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0001361] Anthocyanins [CHEMONTID:0002996] Anthocyanidin-3-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
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[19301817]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[21535810]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[22178178]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[22280831]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flowers	Kunming, China	n.a.	PMID[24621197]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Calyx	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15316	Hibiscus sabdariffa	Species	Malvaceae	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
NPO16038	NPC490466	Raw	n.a.	0.128387094	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO15316	NPC490466	n.a.	Flowers	56.5	n.a.	n.a.	mg/g extract of DW	PMID[22178178]
NPO16038	NPC490466	n.a.	Fruits	0.12	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

☑ 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 NPC490466 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

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 NPC490466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

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