NPASS Compound

Structure

NPC68998 OpenBabel06302215412D 22 23 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 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 -1.7321 -2.0000 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 -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 2 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 C 0 0 0 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 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 2 20 1 0 0 0 0 3 4 1 0 0 0 0 5 4 1 1 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 6 14 1 0 0 0 0 6 7 1 1 0 0 0 6 8 1 0 0 0 0 8 9 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 11 13 1 0 0 0 0 11 14 1 0 0 0 0 14 15 1 1 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 1 0 0 0 17 19 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.29
Volume:	354.944
LogP:	5.109
LogD:	4.482
LogS:	-4.597
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.767
Synthetic Accessibility Score:	4.116
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.544
MDCK Permeability:	1.4864444892737083e-05
Pgp-inhibitor:	0.914
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.733
30% Bioavailability (F30%):	0.543

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.263
Plasma Protein Binding (PPB):	92.69754791259766%
Volume Distribution (VD):	1.279
Pgp-substrate:	6.376513957977295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.239
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.658
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.232
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	7.921
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.905
Carcinogencity:	0.042
Eye Corrosion:	0.988
Eye Irritation:	0.908
Respiratory Toxicity:	0.781

Download Data

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

Natural Product: NPC68998

Natural Product ID:	NPC68998
*Common Name:**	MCHQEVJMCLOQAZ-NDLGOLERSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MCHQEVJMCLOQAZ-NDLGOLERSA-N
Standard InCHI:	InChI=1S/C20H38O2/c1-15(10-14-21)7-8-17-19(4)12-6-11-18(2,3)16(19)9-13-20(17,5)22/h15-17,21-22H,6-14H2,1-5H3/t15-,16+,17-,19+,20-/m0/s1
SMILES:	C[C@@H](CC[C@H]1[C@]2(C)CCCC(C)(C)[C@H]2CC[C@]1(C)O)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	14239432
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[10579879]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844943]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16394535]
NPO21066	Penicillium corylophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456578]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379417]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4087921]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6061704]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8991954]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8991954]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461656]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20945	Uncaria callophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20945	Uncaria callophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19334	Rosa polyantha	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9861	Ophiostoma minus	Species	Ophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17291	Dodonaea lobulata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20063	Euonymus tanakae	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8805	Clavularia frankliniana	Species	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20945	Uncaria callophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21066	Penicillium corylophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18553	Heliopsis helianthoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20123	Actinidia polygama	Species	Actinidiaceae	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 NPC68998 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	399
0.1-0.2	4437
0.2-0.3	18066
0.3-0.4	8849
0.4-0.5	5621
0.5-0.6	3856
0.6-0.7	1185
0.7-0.8	244
0.8-0.85	26
0.85-0.9	11
0.9-0.95	1
0.95-1	2

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 NPC68998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	455
0.1-0.2	4388
0.2-0.3	3074
0.3-0.4	745
0.4-0.5	250
0.5-0.6	187
0.6-0.7	40
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
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