NPASS Compound

Structure

NPC272821 OpenBabel06302215212D 38 42 0 0 1 0 0 0 0 0999 V2000 -2.3602 -3.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8361 -3.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3373 -2.2759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3625 -2.2892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8637 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0129 -0.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8531 -0.4749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8245 -1.4749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6863 -0.9982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6992 -0.0224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5554 0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3923 -0.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3794 -1.0205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2180 -1.5195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2050 -2.4995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0694 -1.0428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9080 -1.5418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7594 -1.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7723 -0.0894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9337 0.4096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9467 1.3896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8018 1.8684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8148 2.8484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9725 3.3496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6699 3.3272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0823 -0.0671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2437 0.4320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6275 0.3894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8951 -2.5218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5295 -1.4974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5684 1.4473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7135 1.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8633 1.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8504 0.4882 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 0.0231 1.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8087 -2.4530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8109 -3.1002 0.0000 C 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 38 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 6 35 1 0 0 0 0 6 7 1 1 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 8 37 1 1 0 0 0 9 10 1 6 0 0 0 9 30 1 0 0 0 0 10 34 2 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 11 31 2 0 0 0 0 12 27 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 13 30 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 26 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 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 23 25 1 0 0 0 0 26 27 1 0 0 0 0 31 32 1 0 0 0 0 32 33 2 0 0 0 0 33 34 1 0 0 0 0 33 36 1 0 0 0 0 34 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.21
Volume:	528.611
LogP:	6.591
LogD:	3.797
LogS:	-3.259
# Rotatable Bonds:	5
TPSA:	129.59
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	4.697
Fsp3:	0.367
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:	-4.998
MDCK Permeability:	1.1005040505551733e-05
Pgp-inhibitor:	0.889
Pgp-substrate:	0.958
Human Intestinal Absorption (HIA):	0.186
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	79.12057495117188%
Volume Distribution (VD):	0.835
Pgp-substrate:	17.822345733642578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.241
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.451
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.836
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.539
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	5.898
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.424
Rat Oral Acute Toxicity:	0.581
Maximum Recommended Daily Dose:	0.218
Skin Sensitization:	0.743
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.223
Respiratory Toxicity:	0.24

Download Data

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

Natural Product: NPC272821

Natural Product ID:	NPC272821
*Common Name:**	QSKLGDOBEUNZLG-SHSRKSKBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QSKLGDOBEUNZLG-SHSRKSKBSA-N
Standard InCHI:	InChI=1S/C30H32O8/c1-14(2)7-6-12-30(5)29(35)27-21-17(10-11-18(31)26(21)38-30)25-28(37-27)23(34)22-20(33)13-19(32)16(24(22)36-25)9-8-15(3)4/h7-8,10-11,13,27,29,31-33,35H,6,9,12H2,1-5H3/t27-,29+,30-/m0/s1
SMILES:	CC(=CCC[C@@]1(C)[C@@H]([C@@H]2c3c(-c4c(c(=O)c5c(cc(c(CC=C(C)C)c5o4)O)O)O2)ccc(c3O1)O)O)C
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:0003520] Pyranoflavonoids

*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
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15165133]
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737271]
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27071	Spirastrella coccinea	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27089	Nectandra glabrescens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28584	Euphorbia indica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27368	Sinularia mayi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27589	Artemisia lehmanniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27280	Stachys spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27147	Habenaria repens	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29149	Zexmenia phyllocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27478	Geodia japonica	Species	Geodiidae	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 NPC272821 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	463
0.1-0.2	1794
0.2-0.3	4147
0.3-0.4	10185
0.4-0.5	8093
0.5-0.6	3763
0.6-0.7	5316
0.7-0.8	4769
0.8-0.85	2480
0.85-0.9	1440
0.9-0.95	245
0.95-1	2

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 NPC272821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	971
0.2-0.3	1845
0.3-0.4	2675
0.4-0.5	1788
0.5-0.6	924
0.6-0.7	366
0.7-0.8	125
0.8-0.85	23
0.85-0.9	24
0.9-0.95	0
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