NPASS Compound

Structure

NPC36218 OpenBabel06302215362D 34 37 0 0 1 0 0 0 0 0999 V2000 3.2874 1.0727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7758 0.2272 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2878 -0.6186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3114 -0.6189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8234 -1.4647 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8470 -1.4649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0015 -1.9534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8467 -0.4885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6919 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6916 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8470 1.4653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 2.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6939 2.9313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 3.9313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 2.4423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3864 2.9308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2322 2.4418 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2319 1.4644 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3858 0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5400 1.4649 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5397 0.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6933 0.9764 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6931 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8464 -0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0978 0.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0984 2.9415 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3119 -2.3102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7523 0.2274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2408 -0.6180 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 2 33 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 32 1 1 0 0 0 6 7 1 1 0 0 0 6 31 1 0 0 0 0 8 6 1 6 0 0 0 8 9 1 0 0 0 0 8 26 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 26 1 0 0 0 0 11 12 1 0 0 0 0 11 30 1 1 0 0 0 12 23 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 17 1 1 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 6 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 0 0 0 0 21 22 1 6 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 26 27 1 6 0 0 0 33 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.31
Volume:	497.581
LogP:	1.468
LogD:	0.263
LogS:	-3.239
# Rotatable Bonds:	6
TPSA:	138.45
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	5.383
Fsp3:	0.889
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:	-5.155
MDCK Permeability:	4.2336478145443834e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.889
Human Intestinal Absorption (HIA):	0.54
20% Bioavailability (F20%):	0.86
30% Bioavailability (F30%):	0.13

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	53.12256622314453%
Volume Distribution (VD):	1.072
Pgp-substrate:	26.69675636291504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.298
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.749
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.143
CYP3A4-substrate:	0.411

ADMET: Excretion

Clearance (CL):	2.6
Half-life (T1/2):	0.601

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.295
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.135
Rat Oral Acute Toxicity:	0.548
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.483
Carcinogencity:	0.15
Eye Corrosion:	0.004
Eye Irritation:	0.045
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC36218

Natural Product ID:	NPC36218
*Common Name:**	JQNVCUBPURTQPQ-SVDHVIHQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JQNVCUBPURTQPQ-SVDHVIHQSA-N
Standard InCHI:	InChI=1S/C27H44O7/c1-15(14-28)5-6-23(32)26(4,33)22-8-10-27(34)17-11-19(29)18-12-20(30)21(31)13-24(18,2)16(17)7-9-25(22,27)3/h11,15-16,18,20-23,28,30-34H,5-10,12-14H2,1-4H3/t15?,16?,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1
SMILES:	CC(CC[C@H]([C@@](C)([C@H]1CC[C@]2(C3=CC(=O)[C@@H]4C[C@H]([C@H](C[C@]4(C)C3CC[C@]12C)O)O)O)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10162877
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives

*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
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11430011]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21612217]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27447736]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32233482]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2775	Cyathula officinalis	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26766	Radix achyranthis bidentatae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2775	Cyathula officinalis	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2775	Cyathula officinalis	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14123	Achyranthes fauriei	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2775	Cyathula officinalis	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8133	Woodwardia orientalis	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2775	Cyathula officinalis	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15077	Achyranthes bidentata	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	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 NPC36218 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	203
0.1-0.2	1288
0.2-0.3	4406
0.3-0.4	8636
0.4-0.5	12604
0.5-0.6	6549
0.6-0.7	5959
0.7-0.8	2698
0.8-0.85	258
0.85-0.9	52
0.9-0.95	16
0.95-1	28

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 NPC36218 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1569
0.2-0.3	3976
0.3-0.4	2277
0.4-0.5	666
0.5-0.6	168
0.6-0.7	149
0.7-0.8	117
0.8-0.85	46
0.85-0.9	10
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