NPASS Compound

Structure

NPC90910 OpenBabel06302216132D 45 49 0 0 1 0 0 0 0 0999 V2000 4.3871 -4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 -3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 -3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -3.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 -3.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0570 -3.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0570 -2.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 -1.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 -0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 2.4122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1192 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8512 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8512 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1192 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 -3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7173 -2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5833 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 -0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 2.4122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6180 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4135 1.9456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6045 2.5334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 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 -2.2226 1.3578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -4.5878 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 6 5 1 6 0 0 0 6 7 1 0 0 0 0 6 33 1 0 0 0 0 7 8 1 0 0 0 0 7 45 1 1 0 0 0 8 9 1 0 0 0 0 8 44 1 6 0 0 0 9 10 1 0 0 0 0 9 34 1 1 0 0 0 10 11 1 6 0 0 0 10 33 1 0 0 0 0 11 12 1 0 0 0 0 12 31 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 14 32 1 0 0 0 0 15 30 2 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 29 1 0 0 0 0 20 25 2 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 27 28 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 35 34 1 1 0 0 0 35 36 1 0 0 0 0 35 41 1 0 0 0 0 36 37 1 0 0 0 0 36 43 1 6 0 0 0 37 38 1 0 0 0 0 37 40 1 0 0 0 0 37 42 1 6 0 0 0 38 39 1 0 0 0 0 40 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	636.17
Volume:	584.273
LogP:	1.32
LogD:	0.305
LogS:	-4.482
# Rotatable Bonds:	10
TPSA:	244.27
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.141
Synthetic Accessibility Score:	4.765
Fsp3:	0.448
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.436
MDCK Permeability:	3.2023082894738764e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.935
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	77.64669036865234%
Volume Distribution (VD):	0.454
Pgp-substrate:	21.478519439697266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.23
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.069

ADMET: Excretion

Clearance (CL):	1.737
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.46
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.671
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.455
Carcinogencity:	0.28
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC90910

Natural Product ID:	NPC90910
*Common Name:**	FGALOZIRMNCSRZ-MIKDDSNXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FGALOZIRMNCSRZ-MIKDDSNXSA-N
Standard InCHI:	InChI=1S/C29H32O16/c1-12(31)40-9-21-23(35)24(36)25(45-28-26(37)29(38,10-30)11-41-28)27(44-21)42-14-6-16(33)22-17(34)8-19(43-20(22)7-14)13-3-4-18(39-2)15(32)5-13/h3-8,21,23-28,30,32-33,35-38H,9-11H2,1-2H3/t21-,23-,24+,25-,26+,27-,28+,29-/m1/s1
SMILES:	CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc(c3c(=O)cc(c4ccc(c(c4)O)OC)oc3c2)O)O1)O[C@H]1[C@@H]([C@@](CO)(CO1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10627850
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
NPO627	Pleurotus ostreatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27134772]
NPO627	Pleurotus ostreatus	Species	Pleurotaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17821	Lactarius atroviridis	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23293	Tadorna ferruginea	Species	Anatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16278	Streptomyces aurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO627	Pleurotus ostreatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22605	Vitis ficifolia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16272	Thalysias juniperina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21073	Aesculus parviflora	Species	Hippocastanaceae	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 NPC90910 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	407
0.1-0.2	1699
0.2-0.3	3583
0.3-0.4	8390
0.4-0.5	9881
0.5-0.6	4787
0.6-0.7	5333
0.7-0.8	5688
0.8-0.85	1963
0.85-0.9	593
0.9-0.95	365
0.95-1	8

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 NPC90910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	903
0.2-0.3	1879
0.3-0.4	2658
0.4-0.5	1947
0.5-0.6	974
0.6-0.7	287
0.7-0.8	125
0.8-0.85	23
0.85-0.9	5
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