NPASS Compound

Structure

NPC37745 OpenBabel06302216152D 48 52 0 0 1 0 0 0 0 0999 V2000 6.1491 -2.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2286 -2.5457 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7496 -3.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2587 -4.1187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8243 -3.4724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1495 -2.8271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2332 -1.8972 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0126 -1.3829 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2039 -1.8498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2039 -3.6936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3952 -1.3829 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3952 -0.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2039 0.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0126 -0.4490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6376 0.3932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9007 -0.1605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4496 -0.9159 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9007 -1.6714 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2213 -2.5467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4785 -2.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0097 -2.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3715 -0.9159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8325 -0.1176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7544 -0.1176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3715 0.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1856 0.7163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5687 1.4014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6670 1.2098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8536 2.2782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5968 -1.8438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7984 -1.3829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7984 -0.4610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.8438 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7984 -1.3829 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7984 -0.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5968 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5968 0.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7984 1.3829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9219 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 -1.5968 -1.8438 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3952 -1.3829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5968 -2.7657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.7657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6302 -0.9393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6443 -0.0057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8428 0.4732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4598 0.4489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 2 18 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 6 5 1 1 0 0 0 6 7 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 45 1 1 0 0 0 8 14 1 0 0 0 0 8 18 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 11 12 1 0 0 0 0 11 30 1 1 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 6 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 1 0 0 0 17 18 1 0 0 0 0 17 22 1 6 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 23 25 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 0 0 0 0 31 32 2 0 0 0 0 31 33 1 0 0 0 0 33 34 1 0 0 0 0 33 44 1 6 0 0 0 34 35 1 0 0 0 0 34 41 1 1 0 0 0 35 40 2 0 0 0 0 35 36 1 0 0 0 0 36 37 2 0 0 0 0 37 38 1 0 0 0 0 38 39 2 0 0 0 0 39 40 1 0 0 0 0 41 42 1 0 0 0 0 41 43 1 0 0 0 0 45 46 1 0 0 0 0 46 47 2 0 0 0 0 46 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	667.34
Volume:	680.897
LogP:	2.884
LogD:	1.773
LogS:	-4.327
# Rotatable Bonds:	12
TPSA:	145.74
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	6.89
Fsp3:	0.649
Lipinski Rule-of-5:	Rejected
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:	-5.374
MDCK Permeability:	7.840441685402766e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.884
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.422

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	46.1439094543457%
Volume Distribution (VD):	1.36
Pgp-substrate:	49.29936981201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.179
CYP2D6-inhibitor:	0.303
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.522
CYP3A4-substrate:	0.75

ADMET: Excretion

Clearance (CL):	4.486
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.864
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.526
Skin Sensitization:	0.029
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC37745

Natural Product ID:	NPC37745
*Common Name:**	XYWMVQVOXQGCCB-RSZAUDQCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XYWMVQVOXQGCCB-RSZAUDQCSA-N
Standard InCHI:	InChI=1S/C37H49NO10/c1-19-26(42)18-25-30(45-21(3)39)37-20(2)27(48-33(44)29(43)28(38(9)10)24-14-12-11-13-15-24)16-17-35(37,8)31(46-22(4)40)32(47-23(5)41)36(19,37)34(25,6)7/h11-15,19,25,27-32,43H,2,16-18H2,1,3-10H3/t19-,25+,27+,28+,29-,30-,31+,32+,35+,36?,37?/m1/s1
SMILES:	C[C@@H]1C(=O)C[C@H]2[C@H](C34C(=C)[C@H](CC[C@@]3(C)[C@H]([C@@H](C14C2(C)C)OC(=O)C)OC(=O)C)OC(=O)[C@@H]([C@H](c1ccccc1)N(C)C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5321432
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes 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
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[15997133]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	PMID[16141313]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17238120]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18405608]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18661821]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21417376]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21627108]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	callus	n.a.	PMID[22368856]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23611151]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[24931277]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562066]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[7700984]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25004	Heracleum yungningense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9075.1	Peucedanum govanianum var. bicolo	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25004	Heracleum yungningense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9075.1	Peucedanum govanianum var. bicolo	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25004	Heracleum yungningense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7067	Stellera chamaejasme	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22273	Angelica pubescens	Species	Apiaceae	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 NPC37745 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	213
0.1-0.2	870
0.2-0.3	2049
0.3-0.4	4812
0.4-0.5	17771
0.5-0.6	14699
0.6-0.7	2162
0.7-0.8	120
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
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 NPC37745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	442
0.2-0.3	892
0.3-0.4	2200
0.4-0.5	3430
0.5-0.6	1781
0.6-0.7	245
0.7-0.8	13
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