NPASS Compound

Structure

NPC166442 OpenBabel06302215302D 27 29 0 0 1 0 0 0 0 0999 V2000 7.9571 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0911 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2250 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2250 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3590 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4930 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6270 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6270 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.4360 -5.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1270 -6.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1270 -6.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5392 -7.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8179 -5.5878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.8669 -5.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6590 -4.3006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7079 -3.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.0135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2431 -2.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1942 -2.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4021 -3.6315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9373 -1.9842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7294 -1.0061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0352 -1.3662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4930 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3590 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3590 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2250 -0.5000 0.0000 C 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 25 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 6 24 2 0 0 0 0 7 8 1 0 0 0 0 8 13 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 2 0 0 0 0 11 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 21 22 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 M END $$$$

Physi-Chem Properties

Molecular Weight:	156.19
Volume:	198.812
LogP:	5.873
LogD:	4.857
LogS:	-5.807
# Rotatable Bonds:	7
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	2.182
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.368
MDCK Permeability:	1.1518922292452771e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.752
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.649
Plasma Protein Binding (PPB):	97.12250518798828%
Volume Distribution (VD):	2.908
Pgp-substrate:	2.4187841415405273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.482
CYP2C19-inhibitor:	0.566
CYP2C19-substrate:	0.583
CYP2C9-inhibitor:	0.456
CYP2C9-substrate:	0.847
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	6.501
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.014
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.848
Carcinogencity:	0.055
Eye Corrosion:	0.993
Eye Irritation:	0.976
Respiratory Toxicity:	0.495

Download Data

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

Natural Product: NPC166442

Natural Product ID:	NPC166442
*Common Name:**	BBULJOHFYQCRDQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BBULJOHFYQCRDQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O6.C7H14O5/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2;1-3-5(9)7(11)6(10)4(2-8)12-3/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3;3-11H,2H2,1H3
SMILES:	COc1ccc(CC2COC(=O)C2Cc2ccc(c(c2)OC)O)cc1OC.CC1C(C(C(C(CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	53399178
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	flower	n.a.	PMID[15481244]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30676026]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9857	Saussurea medusa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19662	Fructus arctii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9857	Saussurea medusa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19805	Forsythia viridissima	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9857	Saussurea medusa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12235	Trachelospermum jasminoides	Species	Apocynaceae	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 NPC166442 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	274
0.1-0.2	1177
0.2-0.3	2661
0.3-0.4	6876
0.4-0.5	12119
0.5-0.6	3835
0.6-0.7	10374
0.7-0.8	4723
0.8-0.85	451
0.85-0.9	173
0.9-0.95	23
0.95-1	11

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 NPC166442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	775
0.2-0.3	1437
0.3-0.4	2343
0.4-0.5	2224
0.5-0.6	1165
0.6-0.7	811
0.7-0.8	151
0.8-0.85	9
0.85-0.9	3
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