Structure

Physi-Chem Properties

Molecular Weight:  277.17
Volume:  283.161
LogP:  0.668
LogD:  0.498
LogS:  -1.901
# Rotatable Bonds:  0
TPSA:  60.77
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.691
Synthetic Accessibility Score:  6.071
Fsp3:  0.812
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:  -4.958
MDCK Permeability:  1.1686851394188125e-05
Pgp-inhibitor:  0.014
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.049
20% Bioavailability (F20%):  0.033
30% Bioavailability (F30%):  0.15

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.904
Plasma Protein Binding (PPB):  22.7027587890625%
Volume Distribution (VD):  1.217
Pgp-substrate:  80.10218811035156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.015
CYP1A2-substrate:  0.123
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.834
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.09
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.626
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.236

ADMET: Excretion

Clearance (CL):  6.957
Half-life (T1/2):  0.738

ADMET: Toxicity

hERG Blockers:  0.333
Human Hepatotoxicity (H-HT):  0.192
Drug-inuced Liver Injury (DILI):  0.04
AMES Toxicity:  0.078
Rat Oral Acute Toxicity:  0.91
Maximum Recommended Daily Dose:  0.98
Skin Sensitization:  0.334
Carcinogencity:  0.791
Eye Corrosion:  0.004
Eye Irritation:  0.032
Respiratory Toxicity:  0.78

Download Data

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

  Natural Product: NPC473232

Natural Product ID:  NPC473232
Common Name*:   MMQTXYOQHYQNGU-WGYQWICLSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MMQTXYOQHYQNGU-WGYQWICLSA-N
Standard InCHI:  InChI=1S/C16H23NO3/c1-9-4-10-6-13(19)12-7-11(18)8-17-3-2-15(20)16(10,12)14(17)5-9/h5,9-12,15,18,20H,2-4,6-8H2,1H3/t9-,10+,11+,12-,15-,16?/m1/s1
SMILES:  CC1CC2CC(=O)C3C24C(CCN(C4=C1)CC(C3)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL376327
PubChem CID:   44424523
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000130] Azaspirodecane 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
NPO32462 lycopodium serratum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[17503851]

☑ 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
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 27900.0 nM PMID[481653]

☑ 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 NPC473232 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.7438 Intermediate Similarity NPC88190
0.7417 Intermediate Similarity NPC476952
0.7381 Intermediate Similarity NPC470539
0.736 Intermediate Similarity NPC476951
0.7281 Intermediate Similarity NPC475239
0.6917 Remote Similarity NPC470534
0.6855 Remote Similarity NPC471109
0.6825 Remote Similarity NPC238323
0.6724 Remote Similarity NPC474348
0.672 Remote Similarity NPC474006
0.6692 Remote Similarity NPC470537
0.6667 Remote Similarity NPC470535
0.6612 Remote Similarity NPC470536
0.661 Remote Similarity NPC98765
0.6587 Remote Similarity NPC96731
0.6583 Remote Similarity NPC176773
0.6565 Remote Similarity NPC280903
0.6557 Remote Similarity NPC470531
0.6557 Remote Similarity NPC470527
0.6557 Remote Similarity NPC470528
0.6557 Remote Similarity NPC470532
0.6557 Remote Similarity NPC470533
0.6557 Remote Similarity NPC470529
0.6557 Remote Similarity NPC470530
0.6496 Remote Similarity NPC45813
0.6481 Remote Similarity NPC278648
0.6481 Remote Similarity NPC476082
0.6446 Remote Similarity NPC475800
0.6439 Remote Similarity NPC317654
0.6439 Remote Similarity NPC96010
0.6417 Remote Similarity NPC212874
0.6406 Remote Similarity NPC35037
0.6379 Remote Similarity NPC289140
0.6372 Remote Similarity NPC312637
0.6364 Remote Similarity NPC202868
0.6341 Remote Similarity NPC274895
0.6341 Remote Similarity NPC474725
0.6333 Remote Similarity NPC265094
0.6325 Remote Similarity NPC184033
0.6324 Remote Similarity NPC133089
0.632 Remote Similarity NPC314550
0.6311 Remote Similarity NPC46981
0.6303 Remote Similarity NPC77703
0.6296 Remote Similarity NPC478139
0.6283 Remote Similarity NPC186688
0.6276 Remote Similarity NPC266697
0.6271 Remote Similarity NPC220111
0.6271 Remote Similarity NPC91604
0.625 Remote Similarity NPC324506
0.6195 Remote Similarity NPC53911
0.6186 Remote Similarity NPC474164
0.6154 Remote Similarity NPC311164
0.6154 Remote Similarity NPC127063
0.6154 Remote Similarity NPC272732
0.6147 Remote Similarity NPC136150
0.6142 Remote Similarity NPC478137
0.6131 Remote Similarity NPC139585
0.6129 Remote Similarity NPC476276
0.6126 Remote Similarity NPC221758
0.6126 Remote Similarity NPC59453
0.6121 Remote Similarity NPC206810
0.6116 Remote Similarity NPC476755
0.6116 Remote Similarity NPC176012
0.6102 Remote Similarity NPC49371
0.6102 Remote Similarity NPC476903
0.6091 Remote Similarity NPC151519
0.6083 Remote Similarity NPC83709
0.6075 Remote Similarity NPC276769
0.6071 Remote Similarity NPC469948
0.6071 Remote Similarity NPC474218
0.6066 Remote Similarity NPC270046
0.6066 Remote Similarity NPC241879
0.6063 Remote Similarity NPC261750
0.6063 Remote Similarity NPC1111
0.6063 Remote Similarity NPC60432
0.6063 Remote Similarity NPC469466
0.6058 Remote Similarity NPC307165
0.6054 Remote Similarity NPC264958
0.6054 Remote Similarity NPC15440
0.6054 Remote Similarity NPC185590
0.6053 Remote Similarity NPC203170
0.6053 Remote Similarity NPC328539
0.605 Remote Similarity NPC190554
0.6048 Remote Similarity NPC271562
0.6047 Remote Similarity NPC470538
0.6047 Remote Similarity NPC288629
0.6032 Remote Similarity NPC63511
0.6018 Remote Similarity NPC474733
0.6018 Remote Similarity NPC145879
0.6018 Remote Similarity NPC20688
0.6018 Remote Similarity NPC474778
0.6018 Remote Similarity NPC31564
0.6018 Remote Similarity NPC474732
0.6018 Remote Similarity NPC51014
0.6017 Remote Similarity NPC472485
0.6017 Remote Similarity NPC174117
0.6016 Remote Similarity NPC477963
0.6016 Remote Similarity NPC119329
0.6 Remote Similarity NPC275740
0.6 Remote Similarity NPC86319
0.6 Remote Similarity NPC114274
0.6 Remote Similarity NPC123912
0.6 Remote Similarity NPC477943
0.5985 Remote Similarity NPC230849
0.5984 Remote Similarity NPC50815
0.5983 Remote Similarity NPC477855
0.5983 Remote Similarity NPC469998
0.5982 Remote Similarity NPC214043
0.5982 Remote Similarity NPC473246
0.5982 Remote Similarity NPC230527
0.5982 Remote Similarity NPC82902
0.5982 Remote Similarity NPC7927
0.5982 Remote Similarity NPC85774
0.5981 Remote Similarity NPC469646
0.5969 Remote Similarity NPC135431
0.5968 Remote Similarity NPC233256
0.5968 Remote Similarity NPC476328
0.5968 Remote Similarity NPC195841
0.5966 Remote Similarity NPC173272
0.5966 Remote Similarity NPC477853
0.5965 Remote Similarity NPC472484
0.5965 Remote Similarity NPC475740
0.5965 Remote Similarity NPC472481
0.5965 Remote Similarity NPC472482
0.5965 Remote Similarity NPC58063
0.5965 Remote Similarity NPC298904
0.5965 Remote Similarity NPC136548
0.5963 Remote Similarity NPC261125
0.5963 Remote Similarity NPC181195
0.5952 Remote Similarity NPC253645
0.5952 Remote Similarity NPC95920
0.5952 Remote Similarity NPC85001
0.5952 Remote Similarity NPC147835
0.595 Remote Similarity NPC474720
0.595 Remote Similarity NPC112167
0.595 Remote Similarity NPC473224
0.595 Remote Similarity NPC218383
0.595 Remote Similarity NPC15390
0.5948 Remote Similarity NPC289213
0.5942 Remote Similarity NPC201359
0.5938 Remote Similarity NPC276995
0.5938 Remote Similarity NPC76660
0.5938 Remote Similarity NPC124358
0.5935 Remote Similarity NPC191892
0.5932 Remote Similarity NPC245972
0.5932 Remote Similarity NPC196485
0.5929 Remote Similarity NPC36350
0.5929 Remote Similarity NPC474083
0.5929 Remote Similarity NPC471224
0.5929 Remote Similarity NPC75810
0.5923 Remote Similarity NPC304646
0.5923 Remote Similarity NPC209252
0.5923 Remote Similarity NPC28280
0.5923 Remote Similarity NPC30196
0.5917 Remote Similarity NPC140300
0.5913 Remote Similarity NPC471722
0.5913 Remote Similarity NPC328313
0.5913 Remote Similarity NPC193360
0.5913 Remote Similarity NPC143767
0.5913 Remote Similarity NPC131470
0.5912 Remote Similarity NPC478136
0.5906 Remote Similarity NPC287764
0.5902 Remote Similarity NPC118275
0.5897 Remote Similarity NPC131872
0.5897 Remote Similarity NPC168027
0.5897 Remote Similarity NPC185936
0.5897 Remote Similarity NPC19114
0.5893 Remote Similarity NPC105173
0.5887 Remote Similarity NPC469958
0.5887 Remote Similarity NPC133420
0.5882 Remote Similarity NPC474371
0.5882 Remote Similarity NPC200702
0.5882 Remote Similarity NPC271195
0.5882 Remote Similarity NPC469599
0.5882 Remote Similarity NPC472932
0.5882 Remote Similarity NPC48330
0.5878 Remote Similarity NPC147707
0.5878 Remote Similarity NPC6531
0.5877 Remote Similarity NPC155011
0.5877 Remote Similarity NPC232156
0.5877 Remote Similarity NPC327115
0.5877 Remote Similarity NPC475022
0.5877 Remote Similarity NPC469994
0.5877 Remote Similarity NPC118648
0.5877 Remote Similarity NPC89077
0.5877 Remote Similarity NPC222613
0.5873 Remote Similarity NPC70235
0.5868 Remote Similarity NPC234542
0.5868 Remote Similarity NPC477854
0.5865 Remote Similarity NPC11379
0.5862 Remote Similarity NPC268406
0.5862 Remote Similarity NPC1015
0.5862 Remote Similarity NPC26959
0.5862 Remote Similarity NPC119416
0.5862 Remote Similarity NPC31985
0.5862 Remote Similarity NPC32830
0.5862 Remote Similarity NPC474245
0.5862 Remote Similarity NPC76879
0.5854 Remote Similarity NPC471083
0.5854 Remote Similarity NPC247060

  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 NPC473232 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.678 Remote Similarity NPD7333 Discontinued
0.6279 Remote Similarity NPD7519 Approved
0.6279 Remote Similarity NPD7517 Approved
0.6279 Remote Similarity NPD7518 Approved
0.6126 Remote Similarity NPD4786 Approved
0.6102 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6091 Remote Similarity NPD3667 Approved
0.609 Remote Similarity NPD7122 Discontinued
0.6061 Remote Similarity NPD6909 Approved
0.6061 Remote Similarity NPD6908 Approved
0.6 Remote Similarity NPD5328 Approved
0.6 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5971 Remote Similarity NPD6845 Suspended
0.5968 Remote Similarity NPD6920 Discontinued
0.5954 Remote Similarity NPD7641 Discontinued
0.594 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5899 Remote Similarity NPD7260 Phase 2
0.5897 Remote Similarity NPD6079 Approved
0.5877 Remote Similarity NPD5279 Phase 3
0.5877 Remote Similarity NPD3618 Phase 1
0.5841 Remote Similarity NPD3133 Approved
0.5841 Remote Similarity NPD3665 Phase 1
0.5841 Remote Similarity NPD3666 Approved
0.5833 Remote Similarity NPD4697 Phase 3
0.5827 Remote Similarity NPD7751 Phase 1
0.5809 Remote Similarity NPD8340 Approved
0.5809 Remote Similarity NPD8342 Approved
0.5809 Remote Similarity NPD8299 Approved
0.5809 Remote Similarity NPD8341 Approved
0.5778 Remote Similarity NPD8080 Discontinued
0.5766 Remote Similarity NPD8451 Approved
0.5748 Remote Similarity NPD6415 Discontinued
0.5735 Remote Similarity NPD7642 Approved
0.5725 Remote Similarity NPD8448 Approved
0.5714 Remote Similarity NPD6399 Phase 3
0.5702 Remote Similarity NPD5222 Approved
0.5702 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5702 Remote Similarity NPD5221 Approved
0.5672 Remote Similarity NPD2132 Phase 3
0.5664 Remote Similarity NPD8415 Approved
0.5656 Remote Similarity NPD5173 Approved
0.5656 Remote Similarity NPD4755 Approved
0.5634 Remote Similarity NPD2613 Approved
0.563 Remote Similarity NPD7148 Clinical (unspecified phase)
0.563 Remote Similarity NPD7147 Phase 3
0.5625 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5603 Remote Similarity NPD8391 Approved
0.5603 Remote Similarity NPD8390 Approved
0.5603 Remote Similarity NPD8392 Approved

  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