NPASS Compound

Structure

NPC260463 OpenBabel06302215222D 55 60 0 0 1 0 0 0 0 0999 V2000 3.3699 0.4690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3699 0.4690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8699 1.3351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3699 2.2011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8699 3.0671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3699 3.9331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3699 4.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3699 3.9331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7821 4.7422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8311 4.4331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8311 3.4331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8365 3.3286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7821 3.1241 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9900 2.1460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2469 1.4768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2958 1.7859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5527 1.1167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5037 0.8077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7606 0.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0175 -0.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 -0.2215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1415 0.7566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1197 0.5487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8106 1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3984 1.4257 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6063 2.4039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1369 3.0730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0879 2.7640 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8800 3.7422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0710 4.0512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 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 -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 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 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 0.8660 1.5000 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2359 4.4331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8699 3.0671 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8699 -0.3970 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 55 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 5 54 1 6 0 0 0 6 7 1 1 0 0 0 6 53 1 0 0 0 0 8 6 1 6 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 28 1 0 0 0 0 11 12 1 1 0 0 0 11 13 1 0 0 0 0 13 14 1 1 0 0 0 14 15 1 0 0 0 0 16 15 1 6 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 25 1 0 0 0 0 17 18 1 6 0 0 0 17 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 25 26 1 6 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 27 30 1 6 0 0 0 28 29 1 6 0 0 0 32 31 1 1 0 0 0 32 33 1 0 0 0 0 32 39 1 0 0 0 0 33 34 1 0 0 0 0 33 42 1 6 0 0 0 34 35 1 0 0 0 0 34 41 1 1 0 0 0 35 36 1 0 0 0 0 35 40 1 6 0 0 0 36 37 1 1 0 0 0 36 39 1 0 0 0 0 37 38 1 0 0 0 0 43 42 1 1 0 0 0 43 44 1 0 0 0 0 43 49 1 0 0 0 0 44 45 1 0 0 0 0 44 52 1 6 0 0 0 45 46 1 0 0 0 0 45 51 1 6 0 0 0 46 47 1 0 0 0 0 46 50 1 1 0 0 0 47 48 1 6 0 0 0 47 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	784.5
Volume:	795.286
LogP:	3.924
LogD:	3.612
LogS:	-3.788
# Rotatable Bonds:	9
TPSA:	218.99
# H-Bond Aceptor:	13
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.121
Synthetic Accessibility Score:	6.067
Fsp3:	0.952
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:	-5.52
MDCK Permeability:	8.32810255815275e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.785
Human Intestinal Absorption (HIA):	0.841
20% Bioavailability (F20%):	0.21
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	79.92960357666016%
Volume Distribution (VD):	0.387
Pgp-substrate:	8.769316673278809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.084
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.389
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	0.962
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.233
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.26
Skin Sensitization:	0.677
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC260463

Natural Product ID:	NPC260463
*Common Name:**	VKPBFUJAJUKRSV-AYYXAYNBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VKPBFUJAJUKRSV-AYYXAYNBSA-N
Standard InCHI:	InChI=1S/C42H72O13/c1-20(2)10-13-27(44)42(9,51)23-14-17-40(7)22(23)11-12-25-39(6)16-15-29(38(4,5)26(39)18-28(45)41(25,40)8)54-37-35(33(49)31(47)24(19-43)53-37)55-36-34(50)32(48)30(46)21(3)52-36/h10,21-37,43-51H,11-19H2,1-9H3/t21-,22+,23-,24+,25+,26-,27+,28-,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40+,41-,42-/m0/s1
SMILES:	CC(=CC[C@H]([C@](C)([C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3C[C@@H]([C@@]21C)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O)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: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
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	Galls	n.a.	n.a.	PMID[16724837]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	gall	n.a.	PMID[17827775]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18854	Jamesonia scammaniae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5621	Arisaema erubescens	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2814	Peperomia amplexicaulis	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1081	Parochetus communis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5621	Arisaema erubescens	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4690	Aphloia theiformis	Species	Aphloiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO957	Sapindus mukorossi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6496	Strongylosoma tambanum	Species	Paradoxosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18854	Jamesonia scammaniae	Species	Pteridaceae	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 NPC260463 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	271
0.1-0.2	1985
0.2-0.3	6222
0.3-0.4	13300
0.4-0.5	9264
0.5-0.6	5356
0.6-0.7	3487
0.7-0.8	1597
0.8-0.85	726
0.85-0.9	276
0.9-0.95	151
0.95-1	62

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 NPC260463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	2135
0.2-0.3	4257
0.3-0.4	1683
0.4-0.5	459
0.5-0.6	245
0.6-0.7	128
0.7-0.8	15
0.8-0.85	5
0.85-0.9	8
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