NPASS Compound

Structure

NPC95796 OpenBabel06302215222D 35 38 0 0 1 0 0 0 0 0999 V2000 -1.6907 3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 4.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0019 3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8481 4.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 3.9111 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5406 4.3996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 2.9339 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5403 2.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 1.4672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4672 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8471 1.4673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8471 2.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7131 2.9449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 2.9339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 2.4448 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8472 3.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6943 0.9782 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6943 1.9782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5408 1.4673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3874 0.9782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3874 0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5409 -0.4890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5409 -1.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6943 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8472 -0.4891 0.0000 C 0 0 0 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2535 -0.4998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 5.3769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0019 5.8654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6906 5.8655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6906 6.8426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5369 5.3769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5369 4.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 3 1 0 0 0 0 2 30 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 1 0 0 0 7 5 1 1 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 10 9 1 6 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 27 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 1 0 0 0 18 25 1 0 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 6 0 0 0 23 24 1 6 0 0 0 23 25 1 0 0 0 0 25 26 1 6 0 0 0 26 27 1 0 0 0 0 27 28 2 0 0 0 0 30 31 1 1 0 0 0 30 32 1 0 0 0 0 32 33 2 0 0 0 0 32 34 1 0 0 0 0 34 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	523.979
LogP:	4.521
LogD:	4.412
LogS:	-4.751
# Rotatable Bonds:	6
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	5.403
Fsp3:	0.767
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:	-4.776
MDCK Permeability:	1.644485746510327e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.905
Human Intestinal Absorption (HIA):	0.224
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.505

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.459
Plasma Protein Binding (PPB):	95.98371124267578%
Volume Distribution (VD):	0.759
Pgp-substrate:	3.029815912246704%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.844
CYP2C19-inhibitor:	0.414
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.709
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.731

ADMET: Excretion

Clearance (CL):	17.39
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.254
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.507
Maximum Recommended Daily Dose:	0.202
Skin Sensitization:	0.035
Carcinogencity:	0.031
Eye Corrosion:	0.01
Eye Irritation:	0.011
Respiratory Toxicity:	0.737

Download Data

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

Natural Product: NPC95796

Natural Product ID:	NPC95796
*Common Name:**	DVWMQGAGJCMGQF-CTOOKQRGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DVWMQGAGJCMGQF-CTOOKQRGSA-N
Standard InCHI:	InChI=1S/C30H44O5/c1-16(18(3)28(34)35-7)8-9-17(2)20-10-11-21-26-24(32)14-22-19(4)23(31)12-13-29(22,5)27(26)25(33)15-30(20,21)6/h17-23,31H,1,8-15H2,2-7H3/t17-,18+,19+,20-,21-,22-,23-,29+,30-/m1/s1
SMILES:	C=C(CC[C@@H](C)[C@H]1CC[C@@H]2C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@H]([C@@H](C)[C@H]1CC3=O)O)[C@H](C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
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 [CHEMONTID:0000260] Monohydroxy 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
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
NPO15630	Manduca sexta	Species	Sphingidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8748375]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6926	Colubrina asiatica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11787	Orthosiphon wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6926	Colubrina asiatica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6926	Colubrina asiatica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11557	Echinus miliaris	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27240	Alcyonium grandis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29200	Moquiniastrum paniculatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15630	Manduca sexta	Species	Sphingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11787	Orthosiphon wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4909	Hilliardiella oligocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6533	Dipterocarpus pilosus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17660	Podocarpus lawrencei	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25603	Lycoris x chejuensis	Species	Amaryllidaceae	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 NPC95796 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	175
0.1-0.2	1140
0.2-0.3	4726
0.3-0.4	11351
0.4-0.5	10563
0.5-0.6	6153
0.6-0.7	5609
0.7-0.8	2522
0.8-0.85	275
0.85-0.9	137
0.9-0.95	39
0.95-1	7

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 NPC95796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1506
0.2-0.3	3907
0.3-0.4	2408
0.4-0.5	681
0.5-0.6	183
0.6-0.7	141
0.7-0.8	133
0.8-0.85	40
0.85-0.9	2
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