NPASS Compound

Structure

NPC116161 OpenBabel06302215592D 32 35 0 0 1 0 0 0 0 0999 V2000 4.5604 -0.6075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6044 -0.4047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3021 0.5246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9556 1.2511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3461 0.7273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 0.0008 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 1.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8466 1.4663 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8469 2.4702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6935 1.9549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6937 2.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5406 3.4207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3873 2.9316 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3875 3.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2341 3.4202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0796 2.9311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0793 1.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3870 1.9544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5401 1.4658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5398 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2344 4.3969 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3887 4.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0804 4.8850 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 5.8617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9261 4.3964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0437 1.6566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 5 6 2 3 0 0 0 5 32 1 0 0 0 0 6 7 1 0 0 0 0 7 25 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 24 1 0 0 0 0 10 11 1 6 0 0 0 10 12 1 0 0 0 0 12 13 1 6 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 15 16 1 6 0 0 0 15 17 1 0 0 0 0 17 18 2 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 20 19 1 6 0 0 0 20 21 1 0 0 0 0 21 22 1 1 0 0 0 22 23 1 0 0 0 0 24 23 1 6 0 0 0 24 25 1 0 0 0 0 25 26 2 0 0 0 0 27 28 1 1 0 0 0 27 29 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.32
Volume:	485.01
LogP:	3.927
LogD:	3.888
LogS:	-4.606
# Rotatable Bonds:	4
TPSA:	49.74
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	4.992
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	1.4791833564231638e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.119

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	85.96782684326172%
Volume Distribution (VD):	0.97
Pgp-substrate:	6.905467987060547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.15
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.275
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.499
CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.855
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.756

ADMET: Excretion

Clearance (CL):	8.418
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.349
Drug-inuced Liver Injury (DILI):	0.371
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.321
Carcinogencity:	0.818
Eye Corrosion:	0.004
Eye Irritation:	0.01
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC116161

Natural Product ID:	NPC116161
*Common Name:**	QSIASPXMKRQPDR-DDVRDOFFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QSIASPXMKRQPDR-DDVRDOFFSA-N
Standard InCHI:	InChI=1S/C28H42N2O2/c1-8-17(2)26(32)29-24-14-16-28(5)22-13-15-27(4)20(18(3)30(6)7)11-12-21(27)19(22)9-10-23(28)25(24)31/h8,11,14,18-19,21-23H,9-10,12-13,15-16H2,1-7H3,(H,29,32)/b17-8+/t18-,19-,21-,22-,23-,27+,28+/m0/s1
SMILES:	C/C=C(C)/C(=NC1=CC[C@]2(C)[C@H]3CC[C@]4(C)C(=CC[C@H]4[C@@H]3CC[C@H]2C1=O)[C@H](C)N(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101936590
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10911	Euphorbia peplis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13128	Crotalaria rosenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9527	Dendrodoa grossularia	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4160	Cephalosporium polyaleurum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11838	Euphorbia regis-jubae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7351	Uncaria pteropoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2332	Plantago serraria	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18213	Strychnos variabilis	Species	Loganiaceae	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 NPC116161 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	96
0.1-0.2	733
0.2-0.3	8299
0.3-0.4	19721
0.4-0.5	10500
0.5-0.6	3005
0.6-0.7	308
0.7-0.8	28
0.8-0.85	4
0.85-0.9	1
0.9-0.95	2
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 NPC116161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	87
0.1-0.2	375
0.2-0.3	2096
0.3-0.4	4793
0.4-0.5	1553
0.5-0.6	221
0.6-0.7	24
0.7-0.8	1
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