NPASS Compound

Structure

NPC99678 OpenBabel06302216162D 26 31 0 0 1 0 0 0 0 0999 V2000 5.0616 0.4777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4892 -0.2404 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 4.1535 0.6144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0535 -0.6250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1046 -1.3059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6041 -1.7704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6044 -2.6566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8376 -3.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0706 -2.6570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0703 -1.7709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3027 -1.3280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3025 -0.4424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0694 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8367 -0.4418 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8371 -1.3276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5349 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7676 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7678 -1.3285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5354 -1.7713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5357 -2.6574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3032 -3.1003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 -1.3289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7662 -0.4433 0.0000 C 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 3.8378 -3.9856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5566 -4.5030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 14 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 15 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 8 25 1 0 0 0 0 9 21 1 0 0 0 0 9 10 2 0 0 0 0 10 15 1 0 0 0 0 10 11 1 0 0 0 0 11 19 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 14 13 1 6 0 0 0 14 15 1 0 0 0 0 16 17 1 0 0 0 0 17 24 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 25 26 1 0 0 0 0 M CHG 1 2 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.15
Volume:	352.091
LogP:	0.796
LogD:	0.61
LogS:	-1.457
# Rotatable Bonds:	1
TPSA:	36.92
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	3.903
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.435
MDCK Permeability:	2.1106914573465474e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	64.83641815185547%
Volume Distribution (VD):	2.57
Pgp-substrate:	19.12930679321289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.243
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.721
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.343
CYP3A4-substrate:	0.705

ADMET: Excretion

Clearance (CL):	3.957
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.15
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.618
Rat Oral Acute Toxicity:	0.802
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.039
Carcinogencity:	0.723
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC99678

Natural Product ID:	NPC99678
*Common Name:**	CIRTUANNSSIDGZ-AWEZNQCLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CIRTUANNSSIDGZ-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C21H22NO4/c1-22(2)5-4-11-7-15(23-3)21-19-17-12(6-14(22)18(11)19)8-16-20(26-10-25-16)13(17)9-24-21/h7-8,14H,4-6,9-10H2,1-3H3/q+1/t14-/m0/s1
SMILES:	C[N+]1(C)CCc2cc(c3c4-c5c(C[C@H]1c24)cc1c(c5CO3)OCO1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5321916
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924164]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[14510598]
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	Costa Rica; Bartica, Guyana	n.a.	PMID[16124770]
NPO6984	Brickellia veronicaefolia	Species	Asteraceae	Eukaryota	essential oil	n.a.	n.a.	PMID[16933870]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15623	Thalictrum revolutum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO695	Picea sitchensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22494	Thalictrum rugosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO695	Picea sitchensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22494	Thalictrum rugosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18140	Thalictrum pubescens	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12143	Corydalis solida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15623	Thalictrum revolutum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22494	Thalictrum rugosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20451	Vitex scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8183	Asplenium viviparum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO254	Coreopsis capillacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5089	Abies forrestii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO695	Picea sitchensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6814	Pegaeophyton scapiflorum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22494	Thalictrum rugosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1845	Physocarpus opulifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2531	Daniellia oliveri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3712	Pedicularis olgae	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6984	Brickellia veronicaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22625	Copris tripartitus	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6636	Ophiorrhiza filistipula	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20320	Cryptostegia madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15623	Thalictrum revolutum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12143	Corydalis solida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21985	Koenigia coriaria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4093	Astragalus stipulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18140	Thalictrum pubescens	Species	Ranunculaceae	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 NPC99678 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	364
0.1-0.2	1727
0.2-0.3	7079
0.3-0.4	11124
0.4-0.5	5845
0.5-0.6	11261
0.6-0.7	4307
0.7-0.8	690
0.8-0.85	179
0.85-0.9	104
0.9-0.95	17
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 NPC99678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	777
0.2-0.3	1095
0.3-0.4	2465
0.4-0.5	2356
0.5-0.6	1516
0.6-0.7	563
0.7-0.8	137
0.8-0.85	15
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