NPASS Compound

Structure

NPC75353 OpenBabel06302215212D 43 48 0 0 1 0 0 0 0 0999 V2000 2.7007 2.6519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.1621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7007 0.6927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8524 1.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8524 2.1621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0040 2.6519 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.1557 2.1621 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6927 2.6519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6927 3.6315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5410 4.1212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5410 5.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6927 5.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1557 5.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1557 4.1212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0040 3.6315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6927 6.5702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3894 3.6315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1557 1.1825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6927 0.6927 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.2470 1.8854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1191 2.8566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 3.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8013 3.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9292 2.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1520 1.5105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8342 1.7319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5785 3.6744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6389 0.4391 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.8924 -0.5071 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1998 -1.1998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4533 -2.1460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7606 -2.8386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1856 -2.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4391 -1.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2535 -0.9462 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 0.8783 -3.2778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3995 -2.3995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8386 -0.7606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3316 1.1318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7007 -0.2869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3974 0.6927 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 43 1 0 0 0 0 4 5 2 0 0 0 0 4 42 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 16 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 10 15 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 19 20 1 0 0 0 0 20 37 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 26 2 0 0 0 0 21 22 1 0 0 0 0 22 23 2 0 0 0 0 23 24 1 0 0 0 0 24 25 2 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 29 30 1 0 0 0 0 29 41 1 0 0 0 0 30 31 1 0 0 0 0 30 40 1 0 0 0 0 31 36 2 0 0 0 0 31 32 1 0 0 0 0 32 33 2 0 0 0 0 32 39 1 0 0 0 0 33 34 1 0 0 0 0 34 35 2 0 0 0 0 34 38 1 0 0 0 0 35 36 1 0 0 0 0 36 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.14
Volume:	558.733
LogP:	1.845
LogD:	1.929
LogS:	-3.897
# Rotatable Bonds:	4
TPSA:	229.99
# H-Bond Aceptor:	13
# H-Bond Donor:	10
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.153
Synthetic Accessibility Score:	4.768
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:	-6.764
MDCK Permeability:	4.377741788630374e-06
Pgp-inhibitor:	0.059
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	88.63030242919922%
Volume Distribution (VD):	0.365
Pgp-substrate:	7.432370662689209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.437
CYP2C9-substrate:	0.674
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	13.618
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.253
AMES Toxicity:	0.269
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.968
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.91
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC75353

Natural Product ID:	NPC75353
*Common Name:**	HGVVOUNEGQIPMS-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HGVVOUNEGQIPMS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H26O13/c31-14-7-19(35)16-11-25(28(41-23(16)9-14)12-1-3-17(33)20(36)5-12)43-30(13-2-4-18(34)21(37)6-13)29(40)27(39)26-22(38)8-15(32)10-24(26)42-30/h1-10,25,27-29,31-40H,11H2
SMILES:	c1cc(c(cc1C1C(Cc2c(cc(cc2O1)O)O)OC1(c2ccc(c(c2)O)O)C(C(c2c(cc(cc2O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	107876
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins

*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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15739361]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21875098]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[23845552]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	seeds	n.a.	n.a.	PMID[23999046]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24868863]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25089845]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28682072]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Twigs	n.a.	n.a.	PMID[29883114]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	fruit	n.a.	Database[Article]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3690	Vitis amurensis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO3690	Vitis amurensis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9546	Cinamomum cassia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8255	Cinnamomum aromaticum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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 NPC75353 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	516
0.1-0.2	1856
0.2-0.3	5383
0.3-0.4	11416
0.4-0.5	6113
0.5-0.6	4503
0.6-0.7	6239
0.7-0.8	5195
0.8-0.85	1012
0.85-0.9	364
0.9-0.95	90
0.95-1	10

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 NPC75353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	424
0.1-0.2	907
0.2-0.3	2093
0.3-0.4	2672
0.4-0.5	1528
0.5-0.6	880
0.6-0.7	534
0.7-0.8	102
0.8-0.85	7
0.85-0.9	1
0.9-0.95	2
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