NPASS Compound

Structure

NPC64850 OpenBabel06302216222D 41 45 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 3 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -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 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 40 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 4 36 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 34 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 9 30 1 0 0 0 0 10 11 1 0 0 0 0 11 22 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 15 2 0 0 0 0 15 21 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 23 29 1 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 25 26 2 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 28 29 2 0 0 0 0 30 31 1 0 0 0 0 30 32 1 0 0 0 0 32 33 1 0 0 0 0 32 34 1 0 0 0 0 34 35 1 0 0 0 0 36 37 1 0 0 0 0 36 38 1 0 0 0 0 38 39 1 0 0 0 0 38 40 1 0 0 0 0 40 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.16
Volume:	534.737
LogP:	-0.197
LogD:	1.446
LogS:	-3.861
# Rotatable Bonds:	6
TPSA:	228.97
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.174
Synthetic Accessibility Score:	4.612
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.213
MDCK Permeability:	6.389230111381039e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.928
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.169
Plasma Protein Binding (PPB):	79.97757720947266%
Volume Distribution (VD):	0.613
Pgp-substrate:	15.536504745483398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.556
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	1.22
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.674
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.028
Carcinogencity:	0.752
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC64850

Natural Product ID:	NPC64850
*Common Name:**	FKIYLTVJPDLUDL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FKIYLTVJPDLUDL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H30O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-8,10,18,20-29,31-36H,9H2,1H3
SMILES:	CC1C(C(C(C(OCC2C(C(C(C(Oc3cc(c4c(=O)cc(c5ccc(cc5)O)oc4c3)O)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5377847
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/JMPR.9000078]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[12130858]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12802735]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18384095]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014120]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014168]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23540838]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295708]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25102361]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25306330]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26099993]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28156114]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29400471]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30726671]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO9857	Saussurea medusa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9857	Saussurea medusa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28608	Olea europaea	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22258	Chrysanthemum indicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9857	Saussurea medusa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28608	Olea europaea	Species	Oleaceae	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
NPO17752	NPC64850	Dried Or Powder	n.a.	125.0459259	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO28608	NPC64850	Raw	n.a.	1.102000016	n.a.	n.a.	mg/100g	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 NPC64850 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	412
0.1-0.2	1654
0.2-0.3	3750
0.3-0.4	9375
0.4-0.5	9271
0.5-0.6	4764
0.6-0.7	5846
0.7-0.8	5346
0.8-0.85	1406
0.85-0.9	513
0.9-0.95	304
0.95-1	56

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 NPC64850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	896
0.2-0.3	1743
0.3-0.4	2753
0.4-0.5	2005
0.5-0.6	973
0.6-0.7	257
0.7-0.8	127
0.8-0.85	20
0.85-0.9	4
0.9-0.95	7
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