NPASS Compound

Structure

NPC111617 OpenBabel06302215232D 33 36 0 0 1 0 0 0 0 0999 V2000 -0.0043 8.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 8.2890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8404 7.3142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0037 6.8265 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0035 5.8516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 5.3639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 4.3891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6914 3.9014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6912 2.9265 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5350 2.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 1.4636 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8453 0.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9759 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8447 1.4640 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8445 2.4393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 2.9270 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8459 2.4388 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8461 3.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0011 3.9270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6900 0.9763 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6898 1.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5345 1.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3792 0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3795 0.0010 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5350 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6903 0.0005 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6906 -0.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8453 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8659 -0.5003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2457 -0.4987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8409 5.3644 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 2 3 0 0 0 5 6 1 0 0 0 0 5 33 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 18 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 18 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 14 30 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 21 27 1 0 0 0 0 21 22 1 0 0 0 0 21 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 25 32 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 29 30 1 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	463.37
Volume:	502.139
LogP:	3.299
LogD:	3.636
LogS:	-4.338
# Rotatable Bonds:	7
TPSA:	89.79
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	4.908
Fsp3:	0.964
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.849
MDCK Permeability:	4.383778286864981e-05
Pgp-inhibitor:	0.632
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.127
20% Bioavailability (F20%):	0.068
30% Bioavailability (F30%):	0.369

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.452
Plasma Protein Binding (PPB):	82.9856185913086%
Volume Distribution (VD):	0.699
Pgp-substrate:	14.648003578186035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.214
CYP3A4-inhibitor:	0.651
CYP3A4-substrate:	0.325

ADMET: Excretion

Clearance (CL):	14.426
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.388
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.429
Maximum Recommended Daily Dose:	0.65
Skin Sensitization:	0.726
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.084

Download Data

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

Natural Product: NPC111617

Natural Product ID:	NPC111617
*Common Name:**	DAIDKOMWNKGKSP-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DAIDKOMWNKGKSP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H49NO4/c1-6-14-29-23(33)9-7-8-18-10-12-27(4)24-20(15-22(32)28(18,27)5)26(3)13-11-19(30)16-25(26,2)17-21(24)31/h18-22,24,30-32H,6-17H2,1-5H3,(H,29,33)
SMILES:	CCCN=C(CCCC1CCC2(C)C3C(CC(C12C)O)C1(C)CCC(CC1(C)CC3O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	53399153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003238] 7-hydroxysteroids

*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
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24211545]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	Urine	n.a.	n.a.	PMID[6330305]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[932730]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24497	Holothuria leucospilota	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30810	Buthus martensi	Species	Buthidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1902	Mesobuthus martensii	Species	Buthidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24497	Holothuria leucospilota	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15173	Concha meretricis seu cyclinae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30810	Buthus martensi	Species	Buthidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24497	Holothuria leucospilota	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12323	Bos taurus	Species	Bovidae	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 NPC111617 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	119
0.1-0.2	2552
0.2-0.3	18407
0.3-0.4	10544
0.4-0.5	5466
0.5-0.6	4176
0.6-0.7	1148
0.7-0.8	251
0.8-0.85	22
0.85-0.9	8
0.9-0.95	4
0.95-1	0

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 NPC111617 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	83
0.1-0.2	1998
0.2-0.3	5086
0.3-0.4	1365
0.4-0.5	344
0.5-0.6	215
0.6-0.7	37
0.7-0.8	17
0.8-0.85	3
0.85-0.9	2
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