NPASS Compound

Structure

NPC484234 OpenBabel06302215232D 32 34 0 0 1 0 0 0 0 0999 V2000 1.6800 -3.5581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5236 -2.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5900 -2.2121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4336 -1.2244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0369 -1.7096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6449 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5109 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3769 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3769 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5109 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6449 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2429 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1090 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9750 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9750 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1090 3.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2429 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -2.2213 -1.3272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1871 -2.8414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 3 1 0 0 0 0 3 4 2 0 0 0 0 3 32 1 0 0 0 0 4 5 1 0 0 0 0 5 30 1 0 0 0 0 5 6 1 1 0 0 0 5 7 1 0 0 0 0 7 8 2 0 0 0 0 7 31 1 0 0 0 0 8 9 1 0 0 0 0 8 28 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 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 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 21 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 22 27 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 25 26 2 0 0 0 0 26 27 1 0 0 0 0 28 29 2 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.19
Volume:	483.053
LogP:	5.062
LogD:	3.312
LogS:	-4.246
# Rotatable Bonds:	10
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	3.644
Fsp3:	0.321
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	1.2499244803620968e-05
Pgp-inhibitor:	0.733
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	99.22848510742188%
Volume Distribution (VD):	0.946
Pgp-substrate:	0.5914334654808044%

ADMET: Metabolism

CYP1A2-inhibitor:	0.926
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.575
CYP2C9-inhibitor:	0.968
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.436
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.973
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	7.428
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.479
Skin Sensitization:	0.753
Carcinogencity:	0.123
Eye Corrosion:	0.019
Eye Irritation:	0.085
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC484234

Natural Product ID:	NPC484234
*Common Name:**	JFMPMCPHPGDCGL-ZVBLBKCWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JFMPMCPHPGDCGL-ZVBLBKCWSA-N
Standard InCHI:	InChI=1S/C28H30O3S/c1-4-20(2)19-28(3)26(30)25(27(31)32-28)24(29)14-10-5-7-11-21-15-17-23(18-16-21)22-12-8-6-9-13-22/h4,6,8-9,12-13,15-19,30H,1,5,7,10-11,14H2,2-3H3/b20-19+/t28-/m1/s1
SMILES:	C=C/C(=C/[C@]1(C)C(=C(C(=O)CCCCCc2ccc(cc2)c2ccccc2)C(=O)S1)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0003327] Fatty acyl thioesters

*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
NPO40894	0cardia spp.	Species	0cardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27187871]

☑ 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
Kd	2
Others	5

Activity Type	# Activity
Organism	4
Others	1
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		MIC90	=	0.21	ug.mL-1	PMID[27187871]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	=	50.0	ug.mL-1	PMID[27187871]
NPT25741	SINGLE PROTEIN	3-oxoacyl-[acyl-carrier-protein] synthase 2	Staphylococcus aureus	Kd	=	33000.0	nM	PMID[27187871]
NPT25741	SINGLE PROTEIN	3-oxoacyl-[acyl-carrier-protein] synthase 2	Staphylococcus aureus	Kd	=	35200.0	nM	PMID[27187871]
NPT1206	Organism	Yersinia pestis	Yersinia pestis	MIC90	>	250.0	ug.mL-1	PMID[27187871]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	1.0	ug.mL-1	PMID[27187871]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	0.5	ug.mL-1	PMID[27187871]

☑ 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 NPC484234 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	166
0.1-0.2	1458
0.2-0.3	3692
0.3-0.4	14729
0.4-0.5	16386
0.5-0.6	5640
0.6-0.7	550
0.7-0.8	72
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
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 NPC484234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	980
0.2-0.3	1222
0.3-0.4	3318
0.4-0.5	2549
0.5-0.6	801
0.6-0.7	94
0.7-0.8	22
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