NPASS Compound

Structure

NPC4238 OpenBabel06302216042D 62 70 0 0 1 0 0 0 0 0999 V2000 -9.7223 1.8640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7441 1.6560 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4351 0.7050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4569 0.4971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7878 1.2402 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3811 0.3267 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8811 -0.5393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3865 0.4312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1786 1.4094 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1841 1.5139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7774 0.6003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8263 0.2913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0832 0.9604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1321 0.6514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9242 -0.3267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0268 -0.6357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2348 -1.6139 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5084 -2.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4594 -1.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6674 -0.9958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4105 -1.6650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6184 -0.6868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3616 -1.3560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3126 -1.0469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5205 -0.0688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9273 -0.9823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 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 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 C 0 0 1 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 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 1 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 -2.5981 -0.5000 0.0000 O 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 2.3309 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1583 2.6399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9014 1.9708 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6935 0.9926 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7425 0.6836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5346 -0.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9993 1.3527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4367 0.3235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8525 2.2798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3662 3.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0447 1.9094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0968 2.1913 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.0750 2.3992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 0 0 0 2 3 1 0 0 0 0 2 62 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 60 1 0 0 0 0 5 6 1 0 0 0 0 5 61 1 0 0 0 0 6 7 1 6 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 60 1 0 0 0 0 11 10 1 1 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 15 20 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 27 28 1 0 0 0 0 28 29 1 0 0 0 0 28 35 1 0 0 0 0 29 30 1 0 0 0 0 29 49 1 0 0 0 0 30 31 1 0 0 0 0 30 48 1 0 0 0 0 31 32 1 0 0 0 0 31 36 1 0 0 0 0 32 33 1 0 0 0 0 32 35 1 0 0 0 0 33 34 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 37 44 1 0 0 0 0 38 39 1 0 0 0 0 38 47 1 0 0 0 0 39 40 1 0 0 0 0 39 46 1 0 0 0 0 40 41 1 0 0 0 0 40 45 1 0 0 0 0 41 42 1 0 0 0 0 41 44 1 0 0 0 0 42 43 1 0 0 0 0 50 49 1 1 0 0 0 50 51 1 0 0 0 0 50 56 1 0 0 0 0 51 52 1 0 0 0 0 51 59 1 6 0 0 0 52 53 1 0 0 0 0 52 58 1 6 0 0 0 53 54 1 0 0 0 0 53 57 1 1 0 0 0 54 55 1 6 0 0 0 54 56 1 0 0 0 0 61 62 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	883.49
Volume:	858.872
LogP:	2.051
LogD:	2.179
LogS:	-3.248
# Rotatable Bonds:	8
TPSA:	258.71
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	9
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	6.762
Fsp3:	0.956
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:	-6.228
MDCK Permeability:	0.00010212888446403667
Pgp-inhibitor:	0.048
Pgp-substrate:	0.816
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.057
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	60.84185028076172%
Volume Distribution (VD):	0.155
Pgp-substrate:	18.42283821105957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.299
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	0.796
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.668
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.564
Skin Sensitization:	0.834
Carcinogencity:	0.319
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC4238

Natural Product ID:	NPC4238
*Common Name:**	KNLOWJPFLKGYGQ-YIKYYZBWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KNLOWJPFLKGYGQ-YIKYYZBWSA-N
Standard InCHI:	InChI=1S/C45H73NO16/c1-19-8-13-45(46-16-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-35(53)33(51)31(49)21(3)56-40)37(55)38(29(18-48)59-42)60-41-36(54)34(52)32(50)28(17-47)58-41/h6,19-21,23-42,46-55H,7-18H2,1-5H3/t19-,20+,21+,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33-,34+,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O2)NC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	76318695
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal 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
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21524113]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10340	Crepis rubra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9062	Lilium longiflorum Thunb.	Strain	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8173	Lupinus multiflorus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6023	Neurolaena venturana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7703	Xanthorrhoea preissii	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2383	Mimosa acacioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5425	Polygala nyikensis	Species	Polygalaceae	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 NPC4238 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 NPC4238 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