NPASS Compound

Structure

NPC126586 OpenBabel06302215342D 45 51 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8581 -2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8092 -3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8092 -4.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 -4.3781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2704 -3.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6421 2.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3938 1.1814 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4181 0.3686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7978 -0.1571 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1952 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0494 -1.1250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0134 -1.3910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7257 -0.6892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2649 -2.3588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2289 -2.6249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9413 -1.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9052 -2.1891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 -1.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3660 -0.5195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4021 -0.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6897 -0.9553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2813 1.6420 0.0000 O 0 0 0 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 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 5 6 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 7 31 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 10 19 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 19 20 1 0 0 0 0 21 22 1 0 0 0 0 21 45 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 28 1 0 0 0 0 26 27 1 0 0 0 0 28 29 1 0 0 0 0 28 44 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 30 33 1 0 0 0 0 31 32 1 0 0 0 0 33 34 1 0 0 0 0 34 35 2 0 0 0 0 34 36 1 0 0 0 0 36 37 2 0 0 0 0 37 38 1 0 0 0 0 38 43 2 0 0 0 0 38 39 1 0 0 0 0 39 40 2 0 0 0 0 40 41 1 0 0 0 0 41 42 2 0 0 0 0 42 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.3
Volume:	635.206
LogP:	4.078
LogD:	3.308
LogS:	-5.327
# Rotatable Bonds:	7
TPSA:	115.43
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	5.522
Fsp3:	0.568
Lipinski Rule-of-5:	Accepted
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:	-5.167
MDCK Permeability:	2.8329570341156796e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.099
20% Bioavailability (F20%):	0.551
30% Bioavailability (F30%):	0.867

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.846
Plasma Protein Binding (PPB):	96.34542083740234%
Volume Distribution (VD):	1.695
Pgp-substrate:	8.750330924987793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.628
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.758
CYP3A4-substrate:	0.414

ADMET: Excretion

Clearance (CL):	4.651
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.603
Human Hepatotoxicity (H-HT):	0.812
Drug-inuced Liver Injury (DILI):	0.644
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.167
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC126586

Natural Product ID:	NPC126586
*Common Name:**	RTIJWSVGYWRMRS-GEBDEUFFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RTIJWSVGYWRMRS-GEBDEUFFSA-N
Standard InCHI:	InChI=1S/C37H44O8/c1-21(38)44-28-17-26-36(4,25-13-12-24(35(25,28)3)23-15-16-42-19-23)33(41)31-32-34(2,20-43-31)27(39)18-29(37(26,32)5)45-30(40)14-11-22-9-7-6-8-10-22/h6-11,13-16,19,24,26-29,31-33,39,41H,12,17-18,20H2,1-5H3/b14-11+/t24-,26-,27+,28-,29-,31+,32-,33+,34+,35-,36-,37-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@](C)(C3=CC[C@@H](c4ccoc4)[C@]13C)[C@@H]([C@H]1[C@H]3[C@](C)(CO1)[C@@H](C[C@@H]([C@]23C)OC(=O)/C=C/c1ccccc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	21581581
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932.1	Melia azedarach var. toosendan	Varieties	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932	Melia azedarach	Species	Meliaceae	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 NPC126586 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	355
0.1-0.2	1342
0.2-0.3	2743
0.3-0.4	5187
0.4-0.5	10171
0.5-0.6	9019
0.6-0.7	9044
0.7-0.8	4311
0.8-0.85	371
0.85-0.9	128
0.9-0.95	25
0.95-1	1

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 NPC126586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	786
0.2-0.3	1596
0.3-0.4	2588
0.4-0.5	2272
0.5-0.6	1125
0.6-0.7	396
0.7-0.8	71
0.8-0.85	5
0.85-0.9	1
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