NPASS Compound

Structure

NPC60911 OpenBabel06302215542D 42 47 0 0 1 0 0 0 0 0999 V2000 3.4755 1.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4755 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3444 -0.5016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3444 -1.5049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2132 -2.0066 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7817 -1.2241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4717 -0.2700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7015 -1.5230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7015 -2.4901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5391 -2.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3779 -1.5237 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2166 -1.0401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0547 -1.5246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8934 -1.0410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8940 -0.0729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.7325 0.4102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7328 1.3779 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8946 1.8624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0562 1.3793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0559 0.4117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1902 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2172 -0.0719 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3795 0.4124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5408 -0.0712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5402 -1.0394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6745 -0.5389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5990 1.8775 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7817 -2.7890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3444 -2.5082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6066 -0.5016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7377 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8689 -0.5016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8689 -1.5049 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -2.0066 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8689 -1.5049 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8689 -0.5016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7377 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7377 1.0033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7377 -2.0066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7377 -2.0066 0.0000 O 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 30 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 28 1 0 0 0 0 5 6 1 0 0 0 0 5 29 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 8 9 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 28 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 15 14 1 6 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 6 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 6 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 30 31 1 0 0 0 0 32 31 1 1 0 0 0 32 33 1 0 0 0 0 32 39 1 0 0 0 0 33 34 1 0 0 0 0 33 42 1 0 0 0 0 34 35 1 0 0 0 0 34 41 1 0 0 0 0 35 36 1 0 0 0 0 35 40 1 6 0 0 0 36 37 1 1 0 0 0 36 39 1 0 0 0 0 37 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	595.41
Volume:	609.304
LogP:	3.177
LogD:	4.088
LogS:	-3.814
# Rotatable Bonds:	7
TPSA:	154.86
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	5.407
Fsp3:	1.0
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:	-5.574
MDCK Permeability:	3.8332964322762564e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.817
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	58.01481246948242%
Volume Distribution (VD):	0.555
Pgp-substrate:	17.002178192138672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.148
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.308
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	5.172
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.984
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.656
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.327
Maximum Recommended Daily Dose:	0.089
Skin Sensitization:	0.964
Carcinogencity:	0.314
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC60911

Natural Product ID:	NPC60911
*Common Name:**	YEWUMIMAJWFDQG-GJCQDAQXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YEWUMIMAJWFDQG-GJCQDAQXSA-N
Standard InCHI:	InChI=1S/C33H57NO8/c1-17(16-40-30-29(38)28(37)27(36)25(15-35)41-30)7-12-33(39)18(2)26-24(42-33)14-23-21-6-5-19-13-20(34)8-10-31(19,3)22(21)9-11-32(23,26)4/h17-30,35-39H,5-16,34H2,1-4H3/t17-,18+,19+,20+,21-,22+,23+,24+,25-,26+,27-,28?,29?,30-,31+,32+,33-/m1/s1
SMILES:	C[C@H](CC[C@@]1([C@@H](C)[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@H]5C[C@H](CC[C@]5(C)[C@H]4CC[C@]23C)N)O1)O)CO[C@H]1C(C([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	52931419
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

*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
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94986-0]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11830167]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	flower	n.a.	PMID[17679444]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20586436]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24913660]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759160]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28183	Cymbopogon flexuosus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10398	Myrica gale	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28183	Cymbopogon flexuosus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10398	Myrica gale	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10398	Myrica gale	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18673	Rhododendron anthopogonoides	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO96	Rhododendron capitatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28183	Cymbopogon flexuosus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10219	Juniperus communis	Species	Cupressaceae	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 NPC60911 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	238
0.1-0.2	4055
0.2-0.3	16410
0.3-0.4	11248
0.4-0.5	5916
0.5-0.6	3302
0.6-0.7	1128
0.7-0.8	327
0.8-0.85	73
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 NPC60911 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	2719
0.2-0.3	4561
0.3-0.4	1136
0.4-0.5	413
0.5-0.6	163
0.6-0.7	30
0.7-0.8	7
0.8-0.85	1
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