Structure

Physi-Chem Properties

Molecular Weight:  347.17
Volume:  341.436
LogP:  2.698
LogD:  3.038
LogS:  -3.501
# Rotatable Bonds:  2
TPSA:  64.3
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.887
Synthetic Accessibility Score:  5.413
Fsp3:  0.684
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:  -4.849
MDCK Permeability:  3.432670564507134e-05
Pgp-inhibitor:  0.08
Pgp-substrate:  0.215
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.017
30% Bioavailability (F30%):  0.6

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.985
Plasma Protein Binding (PPB):  67.0966567993164%
Volume Distribution (VD):  2.101
Pgp-substrate:  32.33195114135742%

ADMET: Metabolism

CYP1A2-inhibitor:  0.353
CYP1A2-substrate:  0.823
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.814
CYP2C9-inhibitor:  0.046
CYP2C9-substrate:  0.144
CYP2D6-inhibitor:  0.187
CYP2D6-substrate:  0.602
CYP3A4-inhibitor:  0.162
CYP3A4-substrate:  0.555

ADMET: Excretion

Clearance (CL):  10.67
Half-life (T1/2):  0.458

ADMET: Toxicity

hERG Blockers:  0.072
Human Hepatotoxicity (H-HT):  0.613
Drug-inuced Liver Injury (DILI):  0.568
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.875
Maximum Recommended Daily Dose:  0.111
Skin Sensitization:  0.321
Carcinogencity:  0.246
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.91

Download Data

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

  Natural Product: NPC43648

Natural Product ID:  NPC43648
Common Name*:   Stemocurtisine
IUPAC Name:   n.a.
Synonyms:   Stemocurtisine
Standard InCHIKey:  LXAQGNNSRKLTLE-KDZIKLRDSA-N
Standard InCHI:  InChI=1S/C19H25NO5/c1-10-13-14-12-6-4-8-20(14)9-5-7-19(13,24-12)25-16(10)17-15(22-3)11(2)18(21)23-17/h10,12-14H,4-9H2,1-3H3/b17-16-/t10-,12-,13+,14-,19+/m0/s1
SMILES:  COC1=C(C)C(=O)O/C/1=C/1O[C@@]23[C@H]([C@@H]1C)[C@@H]1[C@@H](O3)CCCN1CCC2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL467208
PubChem CID:   11035419
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001816] Furofurans

*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
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. n.a. n.a. PMID[15104502]
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. n.a. n.a. PMID[21049906]
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. root n.a. PMID[21049906]
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. rhizome n.a. PMID[21902195]
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. tuberous root n.a. PMID[21902195]
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. n.a. n.a. PMID[21902195]
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1235 Stemona curtisii Species Stemonaceae 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
NPT204 Individual Protein Acetylcholinesterase Homo sapiens MIC > 1000.0 ng PMID[475402]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens MIC > 2.88 nM PMID[475402]
NPT4944 Organism Anopheles minimus Anopheles minimus LC50 = 18.0 ppm PMID[475401]

☑ 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 NPC43648 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
0.9626 High Similarity NPC469997
0.9626 High Similarity NPC65045
0.9279 High Similarity NPC470000
0.9035 High Similarity NPC469999
0.8761 High Similarity NPC477986
0.8761 High Similarity NPC138534
0.8644 High Similarity NPC173173
0.8462 Intermediate Similarity NPC293550
0.8462 Intermediate Similarity NPC477990
0.8462 Intermediate Similarity NPC111162
0.8462 Intermediate Similarity NPC323168
0.8462 Intermediate Similarity NPC477989
0.8319 Intermediate Similarity NPC477987
0.8319 Intermediate Similarity NPC329401
0.8083 Intermediate Similarity NPC471087
0.8083 Intermediate Similarity NPC477985
0.8083 Intermediate Similarity NPC326386
0.8049 Intermediate Similarity NPC477988
0.7899 Intermediate Similarity NPC11379
0.7886 Intermediate Similarity NPC471086
0.7603 Intermediate Similarity NPC230849
0.7583 Intermediate Similarity NPC174463
0.7521 Intermediate Similarity NPC58281
0.7027 Intermediate Similarity NPC469998
0.6864 Remote Similarity NPC75523
0.6838 Remote Similarity NPC473289
0.6818 Remote Similarity NPC215507
0.6818 Remote Similarity NPC307165
0.6807 Remote Similarity NPC93179
0.6746 Remote Similarity NPC235625
0.6723 Remote Similarity NPC44514
0.6716 Remote Similarity NPC133089
0.6694 Remote Similarity NPC130124
0.6694 Remote Similarity NPC193471
0.6637 Remote Similarity NPC110875
0.6637 Remote Similarity NPC118844
0.6637 Remote Similarity NPC72183
0.6637 Remote Similarity NPC299808
0.656 Remote Similarity NPC475988
0.6508 Remote Similarity NPC474984
0.6484 Remote Similarity NPC201889
0.6484 Remote Similarity NPC106791
0.6484 Remote Similarity NPC284656
0.648 Remote Similarity NPC474995
0.6475 Remote Similarity NPC250187
0.6462 Remote Similarity NPC23963
0.6446 Remote Similarity NPC133420
0.6441 Remote Similarity NPC270813
0.6435 Remote Similarity NPC471483
0.6423 Remote Similarity NPC287572
0.6423 Remote Similarity NPC474969
0.6423 Remote Similarity NPC476034
0.6423 Remote Similarity NPC471636
0.64 Remote Similarity NPC47857
0.64 Remote Similarity NPC168758
0.64 Remote Similarity NPC316984
0.64 Remote Similarity NPC30911
0.64 Remote Similarity NPC181510
0.6397 Remote Similarity NPC120335
0.6341 Remote Similarity NPC271562
0.6339 Remote Similarity NPC469860
0.6339 Remote Similarity NPC469861
0.6339 Remote Similarity NPC130436
0.6328 Remote Similarity NPC477554
0.6328 Remote Similarity NPC30196
0.632 Remote Similarity NPC470527
0.632 Remote Similarity NPC470530
0.632 Remote Similarity NPC470533
0.632 Remote Similarity NPC470532
0.632 Remote Similarity NPC470529
0.632 Remote Similarity NPC470528
0.632 Remote Similarity NPC470531
0.6311 Remote Similarity NPC469604
0.6311 Remote Similarity NPC64168
0.6279 Remote Similarity NPC6531
0.6279 Remote Similarity NPC477553
0.6271 Remote Similarity NPC471843
0.626 Remote Similarity NPC101106
0.626 Remote Similarity NPC135216
0.6241 Remote Similarity NPC316133
0.6241 Remote Similarity NPC318445
0.6231 Remote Similarity NPC477555
0.623 Remote Similarity NPC279833
0.623 Remote Similarity NPC80439
0.623 Remote Similarity NPC173690
0.623 Remote Similarity NPC6271
0.6222 Remote Similarity NPC314282
0.622 Remote Similarity NPC261750
0.622 Remote Similarity NPC279383
0.622 Remote Similarity NPC60432
0.622 Remote Similarity NPC1111
0.619 Remote Similarity NPC127578
0.6186 Remote Similarity NPC471492
0.6186 Remote Similarity NPC150041
0.6179 Remote Similarity NPC477000
0.6179 Remote Similarity NPC477001
0.6148 Remote Similarity NPC474244
0.6142 Remote Similarity NPC29501
0.6134 Remote Similarity NPC473333
0.6129 Remote Similarity NPC471844
0.6121 Remote Similarity NPC471184
0.6119 Remote Similarity NPC314629
0.6111 Remote Similarity NPC474891
0.6103 Remote Similarity NPC476951
0.6094 Remote Similarity NPC273215
0.6094 Remote Similarity NPC268327
0.6094 Remote Similarity NPC295444
0.6083 Remote Similarity NPC2666
0.6083 Remote Similarity NPC52820
0.6083 Remote Similarity NPC471490
0.6083 Remote Similarity NPC476344
0.6074 Remote Similarity NPC321197
0.6074 Remote Similarity NPC313342
0.6074 Remote Similarity NPC313333
0.6074 Remote Similarity NPC314512
0.6074 Remote Similarity NPC314451
0.6063 Remote Similarity NPC469603
0.6043 Remote Similarity NPC316401
0.6034 Remote Similarity NPC242877
0.6034 Remote Similarity NPC64913
0.6033 Remote Similarity NPC203627
0.6028 Remote Similarity NPC471256
0.6016 Remote Similarity NPC470534
0.6014 Remote Similarity NPC315387
0.6014 Remote Similarity NPC316205
0.5986 Remote Similarity NPC297058
0.5957 Remote Similarity NPC120420
0.595 Remote Similarity NPC153559
0.5942 Remote Similarity NPC478136
0.5932 Remote Similarity NPC470520
0.5929 Remote Similarity NPC170286
0.592 Remote Similarity NPC205176
0.592 Remote Similarity NPC307846
0.592 Remote Similarity NPC305157
0.5915 Remote Similarity NPC99864
0.5912 Remote Similarity NPC474371
0.5906 Remote Similarity NPC470535
0.5906 Remote Similarity NPC474099
0.5902 Remote Similarity NPC473307
0.5902 Remote Similarity NPC124181
0.5899 Remote Similarity NPC470539
0.5882 Remote Similarity NPC315783
0.5882 Remote Similarity NPC473520
0.5878 Remote Similarity NPC106446
0.5873 Remote Similarity NPC82251
0.5873 Remote Similarity NPC239961
0.5868 Remote Similarity NPC173329
0.5868 Remote Similarity NPC288350
0.5865 Remote Similarity NPC476956
0.5859 Remote Similarity NPC470536
0.5857 Remote Similarity NPC478139
0.5854 Remote Similarity NPC469402
0.5854 Remote Similarity NPC26597
0.5847 Remote Similarity NPC80875
0.5847 Remote Similarity NPC3436
0.5847 Remote Similarity NPC159568
0.5846 Remote Similarity NPC276995
0.5846 Remote Similarity NPC469466
0.5846 Remote Similarity NPC76660
0.584 Remote Similarity NPC474827
0.584 Remote Similarity NPC68001
0.584 Remote Similarity NPC265094
0.584 Remote Similarity NPC199831
0.584 Remote Similarity NPC474828
0.5833 Remote Similarity NPC470994
0.5833 Remote Similarity NPC230889
0.5833 Remote Similarity NPC470521
0.5821 Remote Similarity NPC67917
0.5821 Remote Similarity NPC314268
0.5821 Remote Similarity NPC477515
0.5821 Remote Similarity NPC313802
0.582 Remote Similarity NPC241426
0.5814 Remote Similarity NPC122926
0.5814 Remote Similarity NPC113012
0.5809 Remote Similarity NPC287236
0.5806 Remote Similarity NPC219038
0.5806 Remote Similarity NPC474348
0.5806 Remote Similarity NPC474873
0.5806 Remote Similarity NPC198992
0.5798 Remote Similarity NPC175842
0.5798 Remote Similarity NPC32494
0.5794 Remote Similarity NPC474917
0.5789 Remote Similarity NPC475714
0.5785 Remote Similarity NPC291709
0.5785 Remote Similarity NPC241407
0.5781 Remote Similarity NPC475960
0.5778 Remote Similarity NPC163693
0.5778 Remote Similarity NPC147635
0.5772 Remote Similarity NPC472015
0.5766 Remote Similarity NPC471255
0.5763 Remote Similarity NPC225283
0.576 Remote Similarity NPC121423
0.576 Remote Similarity NPC471599
0.5752 Remote Similarity NPC473339
0.5752 Remote Similarity NPC471552
0.575 Remote Similarity NPC156553
0.575 Remote Similarity NPC238090
0.575 Remote Similarity NPC472195
0.575 Remote Similarity NPC59646
0.575 Remote Similarity NPC475098

  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 NPC43648 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
0.6535 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6412 Remote Similarity NPD8080 Discontinued
0.64 Remote Similarity NPD2204 Approved
0.6357 Remote Similarity NPD7641 Discontinued
0.6336 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6269 Remote Similarity NPD8451 Approved
0.626 Remote Similarity NPD4211 Phase 1
0.6241 Remote Similarity NPD7642 Approved
0.6222 Remote Similarity NPD8448 Approved
0.6204 Remote Similarity NPD8392 Approved
0.6204 Remote Similarity NPD8391 Approved
0.6204 Remote Similarity NPD8390 Approved
0.6176 Remote Similarity NPD8336 Approved
0.6176 Remote Similarity NPD8337 Approved
0.6074 Remote Similarity NPD8342 Approved
0.6074 Remote Similarity NPD8341 Approved
0.6074 Remote Similarity NPD8340 Approved
0.6074 Remote Similarity NPD8299 Approved
0.6029 Remote Similarity NPD8273 Phase 1
0.6 Remote Similarity NPD8338 Approved
0.6 Remote Similarity NPD6845 Suspended
0.5986 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5923 Remote Similarity NPD1376 Discontinued
0.5915 Remote Similarity NPD8415 Approved
0.5882 Remote Similarity NPD7829 Approved
0.5882 Remote Similarity NPD7830 Approved
0.5841 Remote Similarity NPD883 Phase 2
0.5841 Remote Similarity NPD882 Phase 2
0.5794 Remote Similarity NPD6704 Discontinued
0.5772 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5738 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5735 Remote Similarity NPD8444 Approved
0.5704 Remote Similarity NPD2495 Phase 3
0.5676 Remote Similarity NPD8384 Approved
0.5664 Remote Similarity NPD2613 Approved
0.5655 Remote Similarity NPD3615 Approved
0.5655 Remote Similarity NPD3087 Approved
0.5655 Remote Similarity NPD2572 Clinical (unspecified phase)
0.5655 Remote Similarity NPD2571 Approved
0.5655 Remote Similarity NPD2574 Discontinued
0.5655 Remote Similarity NPD2570 Approved
0.5655 Remote Similarity NPD2573 Approved
0.5655 Remote Similarity NPD3614 Approved
0.5655 Remote Similarity NPD3616 Approved
0.5655 Remote Similarity NPD2566 Approved
0.5655 Remote Similarity NPD4745 Approved
0.5655 Remote Similarity NPD3089 Approved
0.5655 Remote Similarity NPD3090 Approved
0.5655 Remote Similarity NPD4746 Phase 3
0.5655 Remote Similarity NPD3088 Approved
0.562 Remote Similarity NPD8266 Approved
0.562 Remote Similarity NPD8268 Approved
0.562 Remote Similarity NPD8267 Approved
0.562 Remote Similarity NPD8269 Approved
0.5607 Remote Similarity NPD2694 Approved
0.5607 Remote Similarity NPD2697 Approved
0.5607 Remote Similarity NPD2696 Approved
0.5607 Remote Similarity NPD2695 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