NPASS Compound

Structure

NPC484380 OpenBabel06302215412D 56 56 0 0 1 0 0 0 0 0999 V2000 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -0.0000 1.0000 0.0000 C 0 0 0 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 7.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 8.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 10.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 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 7 2 3 0 0 0 6 56 1 0 0 0 0 8 7 1 6 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 12 13 2 3 0 0 0 12 55 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 1 0 0 0 14 22 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 20 21 1 0 0 0 0 22 23 2 3 0 0 0 22 54 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 1 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 28 2 0 0 0 0 27 29 1 0 0 0 0 30 31 2 3 0 0 0 30 53 1 0 0 0 0 32 31 1 6 0 0 0 32 33 1 0 0 0 0 32 37 1 0 0 0 0 33 34 1 6 0 0 0 33 35 1 0 0 0 0 35 36 1 0 0 0 0 37 38 2 3 0 0 0 37 52 1 0 0 0 0 38 39 1 0 0 0 0 39 40 1 6 0 0 0 39 41 1 0 0 0 0 41 42 2 3 0 0 0 41 51 1 0 0 0 0 42 43 1 0 0 0 0 43 44 1 6 0 0 0 43 48 1 0 0 0 0 44 45 1 0 0 0 0 45 46 1 0 0 0 0 45 47 1 0 0 0 0 48 49 2 0 0 0 0 48 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	788.47
Volume:	816.721
LogP:	4.609
LogD:	1.966
LogS:	-2.838
# Rotatable Bonds:	30
TPSA:	256.18
# H-Bond Aceptor:	16
# H-Bond Donor:	8
# Rings:	1
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.038
Synthetic Accessibility Score:	4.758
Fsp3:	0.65
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:	-6.23
MDCK Permeability:	0.00012484575563576072
Pgp-inhibitor:	0.307
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.935
20% Bioavailability (F20%):	0.918
30% Bioavailability (F30%):	0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	46.45751190185547%
Volume Distribution (VD):	0.515
Pgp-substrate:	22.22893714904785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	1.127
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.122
Skin Sensitization:	0.1
Carcinogencity:	0.079
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.76

Download Data

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

Natural Product: NPC484380

Natural Product ID:	NPC484380
*Common Name:**	HMVMBWBGAVWWPY-OURJAEHKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HMVMBWBGAVWWPY-OURJAEHKSA-N
Standard InCHI:	InChI=1S/C40H64N6O10/c1-9-11-13-18-31(47)45-33(24(5)6)38(53)43-29(22-27-16-14-12-15-17-27)37(52)42-28(19-20-32(48)49)36(51)46-34(25(7)10-2)39(54)41-26(8)35(50)44-30(40(55)56)21-23(3)4/h12,14-17,23-26,28-30,33-34H,9-11,13,18-22H2,1-8H3,(H,41,54)(H,42,52)(H,43,53)(H,44,50)(H,45,47)(H,46,51)(H,48,49)(H,55,56)/t25-,26-,28-,29-,30-,33-,34-/m0/s1
SMILES:	CCCCCC(=N[C@@H](C(C)C)C(=N[C@@H](Cc1ccccc1)C(=N[C@@H](CCC(=O)O)C(=N[C@@H]([C@@H](C)CC)C(=N[C@@H](C)C(=N[C@@H](CC(C)C)C(=O)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
NPO40570	Paraburkholderia rhizoxinica	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32031805]

☑ 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
IC50	9
MIC	7

Activity Type	# Activity
Cell Line	7
Organism	7
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	40000.0	nM	PMID[32031805]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[32031805]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[32031805]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[32031805]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[32031805]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	>	40000.0	nM	PMID[32031805]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	40000.0	nM	PMID[32031805]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100000.0	nM	PMID[32031805]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100000.0	nM	PMID[32031805]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100000.0	nM	PMID[32031805]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100000.0	nM	PMID[32031805]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100000.0	nM	PMID[32031805]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	MIC	>	100000.0	nM	PMID[32031805]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100000.0	nM	PMID[32031805]
NPT2	Others	Unspecified		IC50	>	40000.0	nM	PMID[32031805]

☑ 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 NPC484380 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	106
0.1-0.2	660
0.2-0.3	3447
0.3-0.4	17817
0.4-0.5	17043
0.5-0.6	2766
0.6-0.7	593
0.7-0.8	224
0.8-0.85	16
0.85-0.9	10
0.9-0.95	2
0.95-1	13

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 NPC484380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	94
0.1-0.2	400
0.2-0.3	759
0.3-0.4	2766
0.4-0.5	3311
0.5-0.6	1373
0.6-0.7	393
0.7-0.8	46
0.8-0.85	7
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