NPASS Compound

Structure

NPC136648 OpenBabel06302215532D 42 47 0 0 1 0 0 0 0 0999 V2000 1.6960 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8480 -1.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6960 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 2.4479 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8480 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 5.3854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 4.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 3.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 2.4479 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3919 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9359 0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 1.9583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6960 0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 6.3646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 3.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 0.4896 0.0000 C 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 -1.6960 2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -2.4479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -3.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 3 42 1 0 0 0 0 4 5 2 0 0 0 0 4 41 1 0 0 0 0 5 6 1 0 0 0 0 7 6 1 1 0 0 0 7 8 1 0 0 0 0 7 37 1 0 0 0 0 8 9 1 0 0 0 0 8 40 1 1 0 0 0 9 10 1 0 0 0 0 10 36 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 39 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 38 1 0 0 0 0 14 36 1 0 0 0 0 15 14 1 6 0 0 0 15 16 1 0 0 0 0 15 32 1 0 0 0 0 16 21 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 17 35 1 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 6 0 0 0 23 32 1 0 0 0 0 24 29 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 27 28 2 0 0 0 0 27 31 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 32 33 1 1 0 0 0 36 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.14
Volume:	549.942
LogP:	2.159
LogD:	2.015
LogS:	-4.062
# Rotatable Bonds:	3
TPSA:	220.76
# H-Bond Aceptor:	12
# H-Bond Donor:	10
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.159
Synthetic Accessibility Score:	4.519
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.806
MDCK Permeability:	4.8265587793139275e-06
Pgp-inhibitor:	0.054
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.842
20% Bioavailability (F20%):	0.714
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	85.94072723388672%
Volume Distribution (VD):	0.497
Pgp-substrate:	13.778145790100098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.598
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	17.404
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.707
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.337
Maximum Recommended Daily Dose:	0.242
Skin Sensitization:	0.973
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.922
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC136648

Natural Product ID:	NPC136648
*Common Name:**	XFZJEEAOWLFHDH-HNTGQZGLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XFZJEEAOWLFHDH-HNTGQZGLSA-N
Standard InCHI:	InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29+/m0/s1
SMILES:	c1cc(c(cc1[C@H]1[C@H](Cc2c(cc(c([C@@H]3c4c(cc(cc4O[C@H](c4ccc(c(c4)O)O)[C@H]3O)O)O)c2O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	24823045
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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

Show entries

Search:

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]

Showing 1 to 10 of 66 entries

Previous1 2 3 4 5 6 7Next

☑ 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

Show entries

Search:

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference
No data available in table

Showing 0 to 0 of 0 entries

PreviousNext

☑ 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

Show entries

Search:

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
No data available in table

Showing 0 to 0 of 0 entries

PreviousNext

☑ 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 NPC136648 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	540
0.1-0.2	1744
0.2-0.3	4830
0.3-0.4	11566
0.4-0.5	6377
0.5-0.6	4254
0.6-0.7	6403
0.7-0.8	5525
0.8-0.85	875
0.85-0.9	446
0.9-0.95	101
0.95-1	36

Show entries

Search:

Similarity Score	Similarity Level	Natural Product ID
No data available in table

Showing 0 to 0 of 0 entries

PreviousNext

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 NPC136648 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	880
0.2-0.3	2029
0.3-0.4	2681
0.4-0.5	1562
0.5-0.6	865
0.6-0.7	569
0.7-0.8	111
0.8-0.85	7
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Show entries

Search:

Similarity Score	Similarity Level	Drug ID	Developmental Stage
No data available in table

Showing 0 to 0 of 0 entries

PreviousNext

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