NPASS Compound

Structure

NPC55247 OpenBabel06302215372D 32 35 0 0 1 0 0 0 0 0999 V2000 0.0023 -4.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -4.3943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -4.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8475 -3.4179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6930 -2.9294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0017 -2.9299 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0015 -1.9534 0.0000 C 0 0 1 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 1.6927 -1.9529 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 2 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 -2.5403 2.4423 0.0000 C 0 0 1 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 1 0 0 0 0 0 0 0 0 0 -4.2319 1.4644 0.0000 C 0 0 1 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 1 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 -0.8443 -1.4654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -3.4183 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 4 1 0 0 0 0 4 5 1 1 0 0 0 4 6 1 0 0 0 0 6 7 1 0 0 0 0 6 32 1 1 0 0 0 7 8 1 0 0 0 0 7 31 1 6 0 0 0 8 9 1 6 0 0 0 10 8 1 6 0 0 0 10 11 1 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 13 12 1 6 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 1 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 17 16 1 6 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 22 1 0 0 0 0 22 23 1 6 0 0 0 22 24 1 0 0 0 0 24 25 1 6 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.37
Volume:	493.779
LogP:	5.353
LogD:	5.07
LogS:	-5.122
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	4.829
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	1.7316060620942153e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	94.86957550048828%
Volume Distribution (VD):	0.906
Pgp-substrate:	1.7874464988708496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.268
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.19
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	12.912
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.711
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.769
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.444
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.949
Carcinogencity:	0.332
Eye Corrosion:	0.963
Eye Irritation:	0.132
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC55247

Natural Product ID:	NPC55247
*Common Name:**	VXBLCLVRWCLEOX-BFYSZXNBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VXBLCLVRWCLEOX-BFYSZXNBSA-N
Standard InCHI:	InChI=1S/C28H50O4/c1-15(2)16(3)25(31)26(32)17(4)20-9-10-21-19-8-7-18-13-23(29)24(30)14-28(18,6)22(19)11-12-27(20,21)5/h15-26,29-32H,7-14H2,1-6H3/t16-,17-,18-,19-,20+,21-,22-,23-,24+,25+,26+,27+,28-/m0/s1
SMILES:	CC(C)[C@H](C)[C@H]([C@@H]([C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H]([C@@H](C[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	13870433
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:0001110] Tetrahydroxy 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
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)91122-1]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10714491]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[16933889]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	n.a.	stem	n.a.	PMID[18310955]
NPO1533	Corynespora cassiicola	Species	Corynesporascaceae	Eukaryota	n.a.	Xisha Islands coral reef in the South China Sea	2009-DEC	PMID[25594263]
NPO1533	Corynespora cassiicola	Species	Corynesporascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25594263]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27996259]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6454	Delphinium tatsienense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4947	Tagetes minuta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4947	Tagetes minuta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5314	Sargassum parvivesiculosum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6454	Delphinium tatsienense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6454	Delphinium tatsienense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1533	Corynespora cassiicola	Species	Corynesporascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2553	Adenocarpus commutatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4947	Tagetes minuta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5403	Fagus menziesii	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8197	Scrophularia deserti	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16088	Streptomyces scabiei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2247	Iphiona scabra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6454	Delphinium tatsienense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7759	Penicillium nalgiovensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO421	Polygonum maritimum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23693	Alseodaphne semecarpifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4112	Ficus fistulosa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5260	Osteospermum thodei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5105	Lagenaria siceraria	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7604	Viguiera lanceolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3111	Daphnandra micrantha	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5314	Sargassum parvivesiculosum	Species	Sargassaceae	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 NPC55247 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	361
0.1-0.2	4244
0.2-0.3	16421
0.3-0.4	9602
0.4-0.5	4744
0.5-0.6	4530
0.6-0.7	2126
0.7-0.8	499
0.8-0.85	90
0.85-0.9	59
0.9-0.95	21
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 NPC55247 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	4214
0.2-0.3	3262
0.3-0.4	761
0.4-0.5	240
0.5-0.6	210
0.6-0.7	66
0.7-0.8	24
0.8-0.85	8
0.85-0.9	0
0.9-0.95	1
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