NPASS Compound

Structure

NPC211235 OpenBabel06302215212D 33 37 0 0 1 0 0 0 0 0999 V2000 3.2336 0.4267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3162 0.6722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0701 1.5895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6448 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6451 -0.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8234 -1.4246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9497 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8226 -1.4251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6457 -0.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6460 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3357 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8231 0.4749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8234 1.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6465 1.9001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4694 1.4247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2919 1.8996 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4472 2.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2925 2.8494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1153 3.3238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9376 2.8485 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9370 1.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9218 1.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4289 1.0455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1142 1.4242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1139 0.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2914 -0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4691 0.4744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4688 -0.5013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7907 3.3404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0005 -1.8994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8669 -2.2859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7690 -2.4574 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 4 2 1 6 0 0 0 4 5 1 0 0 0 0 4 30 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 30 1 0 0 0 0 7 8 1 0 0 0 0 7 31 1 1 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 27 1 0 0 0 0 10 11 1 6 0 0 0 10 12 1 0 0 0 0 12 13 2 0 0 0 0 13 14 1 0 0 0 0 15 14 1 1 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 24 1 0 0 0 0 16 17 1 1 0 0 0 16 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 24 25 1 1 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 1 0 0 0 30 12 1 1 0 0 0 31 32 2 0 0 0 0 31 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	6.469
LogD:	5.227
LogS:	-4.962
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	4.725
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.366
MDCK Permeability:	8.805965990177356e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.657
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	97.0588150024414%
Volume Distribution (VD):	0.621
Pgp-substrate:	2.467146635055542%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.281
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.568
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.508

ADMET: Excretion

Clearance (CL):	3.321
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.632
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.101
Carcinogencity:	0.038
Eye Corrosion:	0.158
Eye Irritation:	0.064
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC211235

Natural Product ID:	NPC211235
*Common Name:**	KOQBBUWNLZFEMV-SXDGTAOVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KOQBBUWNLZFEMV-SXDGTAOVSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t19-,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
SMILES:	CC(C)[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	13996060
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[12951487]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16870425]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24013342]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9846	Argyranthemum frutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26636	Hakea amplexicaulis	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28618	Ursinia alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8128	Malacosoma americanum	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26484	Reniera cratera	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13980	Euphorbia polygonifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21940	Achillea arabica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20727	Myliobatis aquila	Species	Myliobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25757	Meliosma lanceolata	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26688	Pterogorgia bipinnata	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11737	Henricia aspera	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4025	Morina longifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26120	Catharsius molossus	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO536	Dryopteris crassirhizoma	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9846	Argyranthemum frutescens	Species	Asteraceae	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 NPC211235 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	172
0.1-0.2	1145
0.2-0.3	5075
0.3-0.4	15156
0.4-0.5	7225
0.5-0.6	5510
0.6-0.7	4451
0.7-0.8	3108
0.8-0.85	641
0.85-0.9	192
0.9-0.95	19
0.95-1	3

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 NPC211235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1436
0.2-0.3	4031
0.3-0.4	2394
0.4-0.5	625
0.5-0.6	180
0.6-0.7	133
0.7-0.8	163
0.8-0.85	30
0.85-0.9	6
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