NPASS Compound

Structure

NPC487752 OpenBabel06302215502D 44 50 0 0 1 0 0 0 0 0999 V2000 3.2890 1.8134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2890 2.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4347 3.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5804 2.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5804 1.8134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3614 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3614 0.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5804 0.0098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7994 0.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7994 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0127 1.8241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7744 2.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5738 1.8253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3548 2.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1358 1.8253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1358 0.9235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3548 0.4725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6462 -0.5139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3548 -0.4293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1358 -0.8802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9168 -0.4293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7711 -0.9225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9168 0.4725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9032 0.4725 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7575 -0.0207 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7575 -1.0071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6118 -1.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1050 -2.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1186 -2.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4661 -1.0071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4661 -0.0207 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3204 0.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3204 1.4590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4661 1.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1747 1.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6118 0.4725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9032 -1.5004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4100 1.3268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5738 0.9235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5738 -0.0371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7868 0.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8444 1.9099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1433 3.2930 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 44 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 10 2 0 0 0 0 5 6 1 0 0 0 0 6 7 2 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 42 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 41 2 0 0 0 0 11 12 1 0 0 0 0 13 12 1 1 0 0 0 13 14 1 0 0 0 0 13 39 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 23 1 0 0 0 0 16 17 1 0 0 0 0 16 43 1 1 0 0 0 17 18 1 6 0 0 0 17 19 1 0 0 0 0 17 39 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 23 21 1 1 0 0 0 23 38 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 24 38 1 1 0 0 0 25 26 1 0 0 0 0 25 36 1 1 0 0 0 26 27 1 0 0 0 0 26 37 1 1 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 30 1 0 0 0 0 30 31 1 0 0 0 0 31 32 1 1 0 0 0 31 36 1 0 0 0 0 32 33 2 0 0 0 0 33 34 1 0 0 0 0 33 35 1 0 0 0 0 39 40 1 1 0 0 0 39 41 1 0 0 0 0 41 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	603.36
Volume:	633.896
LogP:	6.771
LogD:	4.425
LogS:	-4.8
# Rotatable Bonds:	4
TPSA:	104.31
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	6.054
Fsp3:	0.649
Lipinski Rule-of-5:	Rejected
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:	-5.059
MDCK Permeability:	1.1389739484002348e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.767
Plasma Protein Binding (PPB):	91.0396957397461%
Volume Distribution (VD):	1.87
Pgp-substrate:	5.562658786773682%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.798
CYP2C19-inhibitor:	0.557
CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.634
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.498
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.719
CYP3A4-substrate:	0.865

ADMET: Excretion

Clearance (CL):	11.535
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.806
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.536
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.752
Carcinogencity:	0.885
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC487752

Natural Product ID:	NPC487752
*Common Name:**	QZBRONWINVVXQI-FOQDWJSNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QZBRONWINVVXQI-FOQDWJSNSA-N
Standard InCHI:	InChI=1S/C37H49NO6/c1-20(2)12-13-22-10-9-11-25-28(22)24-19-23-14-17-36(41)34(7,35(23,8)30(24)38-25)16-15-26(39)37(36)32(44-37)29-31(40)33(5,6)43-27(42-29)18-21(3)4/h9-12,18,23,27,29,31-32,38,40-41H,13-17,19H2,1-8H3/t23-,27-,29+,31+,32+,34+,35+,36-,37-/m0/s1
SMILES:	CC(=CCc1cccc2c1c1C[C@@H]3CC[C@@]4([C@](C)(CCC(=O)[C@@]54[C@@H]([C@H]4[C@H](C(C)(C)O[C@@H](C=C(C)C)O4)O)O5)[C@@]3(C)c1[nH]2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO41068	Tolypocladium sp. XL115	Strain	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30702286]

☑ 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

Activity Type	# Activity
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	12.5	ug.mL-1	PMID[30702286]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[30702286]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	12.5	ug.mL-1	PMID[30702286]
NPT1398	Organism	Salmonella paratyphi	Salmonella enterica subsp. enterica serovar Paratyphi A	MIC	=	12.5	ug.mL-1	PMID[30702286]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[30702286]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	=	12.5	ug.mL-1	PMID[30702286]

☑ 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 NPC487752 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	389
0.1-0.2	1615
0.2-0.3	3859
0.3-0.4	14084
0.4-0.5	17605
0.5-0.6	3987
0.6-0.7	973
0.7-0.8	150
0.8-0.85	26
0.85-0.9	8
0.9-0.95	0
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 NPC487752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	535
0.2-0.3	758
0.3-0.4	2654
0.4-0.5	3440
0.5-0.6	1299
0.6-0.7	193
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
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