NPASS Compound

Structure

NPC12343 OpenBabel06302215512D 33 38 0 0 1 0 0 0 0 0999 V2000 -1.1513 -2.0095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4596 -1.0602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9020 -0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4594 0.4744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3615 0.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3616 -0.7670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1691 -1.3536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1693 -2.3518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1186 -2.6601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7052 -1.8525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1184 -1.0451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9019 1.2416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 0.9484 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8217 1.4229 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6433 0.9482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4646 1.4227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3170 1.9151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4647 2.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8218 2.3713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2861 0.9481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2860 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4643 -0.4745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6431 -0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6430 -0.9846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8215 -0.4743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8214 -1.4229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1065 -1.6200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3997 -2.5222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7412 -0.9150 0.0000 O 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 -0.0001 -0.9803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4642 -1.4548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1352 1.4380 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 6 1 0 0 0 0 2 3 2 0 0 0 0 3 30 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 6 0 0 0 7 11 2 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 18 19 1 0 0 0 0 20 21 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 25 26 1 0 0 0 0 25 30 1 0 0 0 0 26 27 1 0 0 0 0 27 28 2 0 0 0 0 27 29 1 0 0 0 0 30 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.23
Volume:	457.899
LogP:	0.678
LogD:	0.798
LogS:	-3.752
# Rotatable Bonds:	3
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	5.449
Fsp3:	0.731
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:	-5.477
MDCK Permeability:	1.875421730801463e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.326
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277
Plasma Protein Binding (PPB):	91.50980377197266%
Volume Distribution (VD):	1.112
Pgp-substrate:	8.801486015319824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.531
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	3.545
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.449
Human Hepatotoxicity (H-HT):	0.876
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.161
Carcinogencity:	0.012
Eye Corrosion:	0.004
Eye Irritation:	0.032
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC12343

Natural Product ID:	NPC12343
*Common Name:**	QMEMRUDWBPMCGJ-SRSHEJQUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QMEMRUDWBPMCGJ-SRSHEJQUSA-N
Standard InCHI:	InChI=1S/C26H34O7/c1-12-14(13-5-6-31-10-13)7-15-20(12)26(4)16(8-19(29)30)25(3)18(28)9-17(27)24(2)11-32-21(22(24)25)23(26)33-15/h5-6,10,14-18,21-23,27-28H,7-9,11H2,1-4H3,(H,29,30)/t14-,15-,16-,17-,18+,21-,22+,23-,24-,25+,26-/m1/s1
SMILES:	CC1=C2[C@@H](C[C@H]1c1ccoc1)O[C@@H]1[C@H]3[C@H]4[C@](C)(CO3)[C@@H](C[C@@H]([C@]4(C)[C@@H](CC(=O)O)[C@]21C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	185704
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19081726]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23395661]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26224	Walsura piscidia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8783	Stachys palustris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8783	Stachys palustris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2006	Centaurea sinaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26224	Walsura piscidia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1594	[enterobacter] aerogenes	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15379	Phalaenopsis schilleriana	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9217	Daphniphyllum angustifolium	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8783	Stachys palustris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2423	Melochia corchorifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO774	Cleome pungens	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1058	Pestalotiopsis heterocornis	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8249	Marcetella moquiniana	Species	Rosaceae	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 NPC12343 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	328
0.1-0.2	1241
0.2-0.3	2951
0.3-0.4	5159
0.4-0.5	10627
0.5-0.6	10726
0.6-0.7	10142
0.7-0.8	1109
0.8-0.85	281
0.85-0.9	101
0.9-0.95	27
0.95-1	5

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 NPC12343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	877
0.2-0.3	2115
0.3-0.4	2677
0.4-0.5	1971
0.5-0.6	951
0.6-0.7	263
0.7-0.8	12
0.8-0.85	2
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