NPASS Compound

Structure

NPC310783 OpenBabel06302215362D 59 65 0 0 1 0 0 0 0 0999 V2000 -0.0403 3.2336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6036 2.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1697 1.5064 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8275 1.4317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7331 0.6802 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6340 1.1141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6229 1.2631 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6117 1.1141 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9064 2.0696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2263 2.8027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5210 3.7583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8408 4.4913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8659 4.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5712 3.3132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2513 2.5802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1857 5.0018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5127 0.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0760 1.5064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2457 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.9148 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8284 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7239 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7457 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9682 -1.8410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8935 -2.8382 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5282 -3.7690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3942 -4.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2602 -3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1262 -4.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9923 -3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9923 -2.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1262 -2.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2602 -2.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9047 -4.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5848 -5.2839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0784 -5.1142 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6540 -5.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0542 -6.7320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1079 -6.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1229 -5.4089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1229 -5.4089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9738 -6.3978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1673 -5.1142 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8869 -6.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1127 -6.1040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4500 -5.1626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3410 -4.5509 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2824 -3.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1485 -4.2690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6478 -2.8382 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -3.2174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2197 -2.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6940 -1.6039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7225 -1.8410 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4309 -0.5007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9654 -1.7662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3393 2.0696 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 3 4 1 6 0 0 0 5 3 1 6 0 0 0 5 6 1 0 0 0 0 5 56 1 0 0 0 0 6 7 2 3 0 0 0 6 59 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 6 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 10 15 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 19 23 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 23 22 1 6 0 0 0 23 24 1 0 0 0 0 24 25 2 3 0 0 0 24 58 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 6 0 0 0 26 34 1 0 0 0 0 27 28 1 0 0 0 0 28 33 2 0 0 0 0 28 29 1 0 0 0 0 29 30 2 0 0 0 0 30 31 1 0 0 0 0 31 32 2 0 0 0 0 32 33 1 0 0 0 0 34 35 2 0 0 0 0 34 36 1 0 0 0 0 36 40 1 0 0 0 0 36 37 1 0 0 0 0 37 38 1 0 0 0 0 38 39 1 0 0 0 0 40 39 1 6 0 0 0 40 41 1 0 0 0 0 41 42 2 0 0 0 0 41 43 1 0 0 0 0 43 47 1 0 0 0 0 43 44 1 0 0 0 0 44 45 1 0 0 0 0 45 46 1 0 0 0 0 47 46 1 6 0 0 0 47 48 1 0 0 0 0 48 49 2 0 0 0 0 48 50 1 0 0 0 0 50 54 1 0 0 0 0 50 51 1 0 0 0 0 51 52 1 0 0 0 0 52 53 1 0 0 0 0 54 53 1 6 0 0 0 54 55 1 0 0 0 0 55 56 2 3 0 0 0 55 57 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	811.43
Volume:	822.71
LogP:	2.941
LogD:	2.623
LogS:	-3.842
# Rotatable Bonds:	6
TPSA:	188.77
# H-Bond Aceptor:	15
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	5.286
Fsp3:	0.568
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:	-5.841
MDCK Permeability:	1.7091886547859758e-05
Pgp-inhibitor:	0.342
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.976
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	79.16736602783203%
Volume Distribution (VD):	0.595
Pgp-substrate:	9.506745338439941%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.141
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.581
CYP2C9-substrate:	0.484
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.96
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	9.125
Half-life (T1/2):	0.643

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.177
Carcinogencity:	0.272
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.059

Download Data

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

Natural Product: NPC310783

Natural Product ID:	NPC310783
*Common Name:**	CEUJHCJMKAEQNR-IFUGPJDHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CEUJHCJMKAEQNR-IFUGPJDHSA-N
Standard InCHI:	InChI=1S/C44H57N7O8/c1-3-27(2)37-40(55)46-32(26-29-17-19-30(52)20-18-29)41(56)48-21-7-13-33(48)38(53)45-31(25-28-11-5-4-6-12-28)42(57)50-23-9-15-35(50)44(59)51-24-10-16-36(51)43(58)49-22-8-14-34(49)39(54)47-37/h4-6,11-12,17-20,27,31-37,52H,3,7-10,13-16,21-26H2,1-2H3,(H,45,53)(H,46,55)(H,47,54)/t27-,31-,32-,33-,34-,35-,36-,37-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=N[C@@H](Cc2ccc(cc2)O)C(=O)N2CCC[C@H]2C(=N[C@@H](Cc2ccccc2)C(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=N1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	23584398
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO17228	Streptosporangium sibiricum	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21612226]
NPO17228	Streptosporangium sibiricum	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25960001]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13082	Veratrum californicum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13082	Veratrum californicum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13082	Veratrum californicum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5061	Rhaphiolepis indica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11624	Didymella lethalis	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13082	Veratrum californicum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO261	Sulfurospirillum multivorans	Species	Campylobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10821	Magnolia praecocissima	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16568	Vernonia cotoneaster	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17379	Lepidium syvaschicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17927	Streptomyces thioluteus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17228	Streptosporangium sibiricum	Species	Streptosporangiaceae	Bacteria	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 NPC310783 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	253
0.1-0.2	1244
0.2-0.3	7725
0.3-0.4	10010
0.4-0.5	17827
0.5-0.6	4676
0.6-0.7	667
0.7-0.8	248
0.8-0.85	22
0.85-0.9	13
0.9-0.95	7
0.95-1	5

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 NPC310783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	500
0.2-0.3	837
0.3-0.4	1851
0.4-0.5	3723
0.5-0.6	1824
0.6-0.7	241
0.7-0.8	14
0.8-0.85	0
0.85-0.9	1
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