NPASS Compound

Structure

NPC276406 OpenBabel06302215362D 77 84 0 0 1 0 0 0 0 0999 V2000 14.3800 -7.3256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5342 -6.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6883 -7.3256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6883 -8.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8424 -6.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9965 -7.3256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8424 -5.8605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9965 -5.3721 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9965 -4.3953 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1506 -3.9070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8424 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6883 -3.4186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3047 -4.3953 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.3047 -5.3721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1506 -5.8605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6390 -6.7064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6623 -6.7064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4589 -3.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6130 -4.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7671 -3.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7671 -2.9302 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.9212 -2.4419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9212 -3.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0753 -0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5869 -0.1309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5637 -0.1309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 0.7150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9212 -1.4651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.7671 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6130 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6130 -2.4419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3047 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4589 -2.9302 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4589 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3047 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1506 -2.9302 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9965 -2.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -0.9767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6918 -0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8459 -2.4419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6918 -2.9302 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6918 -3.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -4.3953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -4.3953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -2.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -2.4419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 -2.9302 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5377 -2.4419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 -0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 0.4884 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 -0.9767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 -2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -3.9070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 0.4884 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 -1.6918 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8424 -3.9070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6883 -4.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6883 -5.3721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5342 -3.9070 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 3 4 1 0 0 0 0 3 5 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 8 7 1 6 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 74 1 1 0 0 0 10 39 1 0 0 0 0 10 11 1 6 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 18 36 1 0 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 34 1 0 0 0 0 21 22 1 0 0 0 0 22 31 1 0 0 0 0 22 23 1 6 0 0 0 22 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 26 41 1 6 0 0 0 27 28 1 1 0 0 0 27 29 1 0 0 0 0 27 31 1 0 0 0 0 29 30 1 0 0 0 0 31 32 1 0 0 0 0 32 33 1 0 0 0 0 33 34 1 0 0 0 0 34 35 1 6 0 0 0 34 36 1 0 0 0 0 36 37 1 1 0 0 0 36 38 1 0 0 0 0 38 39 1 0 0 0 0 39 40 1 1 0 0 0 42 41 1 6 0 0 0 42 43 1 0 0 0 0 42 50 1 0 0 0 0 43 44 1 0 0 0 0 43 64 1 1 0 0 0 44 45 1 0 0 0 0 44 63 1 6 0 0 0 45 46 1 0 0 0 0 45 51 1 1 0 0 0 46 47 1 6 0 0 0 46 50 1 0 0 0 0 47 48 2 0 0 0 0 47 49 1 0 0 0 0 52 51 1 1 0 0 0 52 53 1 0 0 0 0 52 59 1 0 0 0 0 53 54 1 0 0 0 0 53 62 1 6 0 0 0 54 55 1 0 0 0 0 54 61 1 1 0 0 0 55 56 1 0 0 0 0 55 60 1 6 0 0 0 56 57 1 1 0 0 0 56 59 1 0 0 0 0 57 58 1 0 0 0 0 65 64 1 6 0 0 0 65 66 1 0 0 0 0 65 70 1 0 0 0 0 66 67 1 0 0 0 0 66 73 1 1 0 0 0 67 68 1 0 0 0 0 67 72 1 6 0 0 0 68 69 1 0 0 0 0 68 71 1 1 0 0 0 69 70 1 0 0 0 0 74 75 1 0 0 0 0 75 76 2 0 0 0 0 75 77 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1100.54
Volume:	1063.081
LogP:	1.093
LogD:	0.539
LogS:	-3.06
# Rotatable Bonds:	15
TPSA:	367.81
# H-Bond Aceptor:	23
# H-Bond Donor:	12
# Rings:	8
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.047
Synthetic Accessibility Score:	6.938
Fsp3:	0.87
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.431
MDCK Permeability:	0.0002567018964327872
Pgp-inhibitor:	0.761
Pgp-substrate:	0.88
Human Intestinal Absorption (HIA):	0.992
20% Bioavailability (F20%):	0.268
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	60.06108093261719%
Volume Distribution (VD):	0.274
Pgp-substrate:	10.359724998474121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.081
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	0.711
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.286
Drug-inuced Liver Injury (DILI):	0.189
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.522
Skin Sensitization:	0.042
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.311

Download Data

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

Natural Product: NPC276406

Natural Product ID:	NPC276406
*Common Name:**	MLLNRQWNTKNRGQ-JXJCUFHPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MLLNRQWNTKNRGQ-JXJCUFHPSA-N
Standard InCHI:	InChI=1S/C54H84O23/c1-10-23(2)45(69)77-42-43(71-24(3)58)54(22-57)26(17-49(42,4)5)25-11-12-30-50(6)15-14-32(51(7,21-56)29(50)13-16-52(30,8)53(25,9)18-31(54)60)73-48-40(75-46-36(64)33(61)27(59)20-70-46)38(66)39(41(76-48)44(67)68)74-47-37(65)35(63)34(62)28(19-55)72-47/h10-11,26-43,46-48,55-57,59-66H,12-22H2,1-9H3,(H,67,68)/b23-10+/t26?,27-,28-,29?,30?,31-,32+,33+,34-,35+,36-,37-,38+,39+,40-,41+,42+,43+,46+,47+,48-,50+,51-,52-,53-,54+/m1/s1
SMILES:	C/C=C(C)/C(=O)O[C@H]1[C@@H]([C@@]2(CO)C(CC1(C)C)C1=CCC3[C@@]4(C)CC[C@@H]([C@](C)(CO)C4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46905212
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10579862]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15104496]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25442304]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783160]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29234.1	Aesculus chinensis var. wilsonii	Varieties	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29234.1	Aesculus chinensis var. wilsonii	Varieties	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29234	Aesculus chinensis	Species	Sapindaceae	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

Activity Type	# Activity
Others	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Serum Mg2+ level	=	3.0	n.a.	PMID[531258]
NPT32	Organism	Mus musculus	Mus musculus	Increase	=	-6.3	%	PMID[531258]
NPT32	Organism	Mus musculus	Mus musculus	Serum Mg2+ level	=	3.1	n.a.	PMID[531258]
NPT32	Organism	Mus musculus	Mus musculus	Increase	=	-3.1	%	PMID[531258]
NPT32	Organism	Mus musculus	Mus musculus	Serum Mg2+ level	=	3.6	n.a.	PMID[531258]
NPT32	Organism	Mus musculus	Mus musculus	Increase	=	12.5	%	PMID[531258]
NPT32	Organism	Mus musculus	Mus musculus	Increase	=	3.3	%	PMID[531258]

☑ 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 NPC276406 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

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 NPC276406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

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