Structure

Physi-Chem Properties

Molecular Weight:  421.21
Volume:  410.905
LogP:  1.09
LogD:  1.291
LogS:  -1.357
# Rotatable Bonds:  4
TPSA:  104.35
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.568
Synthetic Accessibility Score:  6.298
Fsp3:  0.727
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.566
MDCK Permeability:  7.451200508512557e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.968
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.246
Plasma Protein Binding (PPB):  74.30718231201172%
Volume Distribution (VD):  2.199
Pgp-substrate:  24.57185935974121%

ADMET: Metabolism

CYP1A2-inhibitor:  0.082
CYP1A2-substrate:  0.781
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.367
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.089
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.174
CYP3A4-inhibitor:  0.06
CYP3A4-substrate:  0.56

ADMET: Excretion

Clearance (CL):  12.097
Half-life (T1/2):  0.931

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.491
Drug-inuced Liver Injury (DILI):  0.422
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.94
Maximum Recommended Daily Dose:  0.85
Skin Sensitization:  0.255
Carcinogencity:  0.712
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.926

Download Data

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

  Natural Product: NPC470000

Natural Product ID:  NPC470000
Common Name*:   Stemocurtisinol N-Oxide
IUPAC Name:   n.a.
Synonyms:   Stemocurtisinol N-Oxide
Standard InCHIKey:  GQHSQVDONZAQMO-UAMZZLTQSA-N
Standard InCHI:  InChI=1S/C22H31NO7/c1-5-14(24)13-7-8-15-17-16-11(2)19(20-18(27-4)12(3)21(25)28-20)30-22(16,29-15)9-6-10-23(13,17)26/h11,13-17,24H,5-10H2,1-4H3/b20-19-/t11-,13-,14-,15-,16+,17-,22+,23?/m0/s1
SMILES:  CC[C@@H]([C@@H]1CC[C@H]2[C@@H]3N1(=O)CCC[C@@]1([C@@H]3[C@H](C)/C(=C3/OC(=O)C(=C3OC)C)/O1)O2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1642207
PubChem CID:   53320016
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 = 100.0 ng PMID[489557]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens MIC = 0.24 nM PMID[489557]

☑ 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 NPC470000 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
0.964 High Similarity NPC65045
0.964 High Similarity NPC469997
0.9279 High Similarity NPC43648
0.8512 High Similarity NPC111162
0.8512 High Similarity NPC323168
0.8512 High Similarity NPC293550
0.8512 High Similarity NPC477989
0.8512 High Similarity NPC477990
0.8443 Intermediate Similarity NPC469999
0.8182 Intermediate Similarity NPC138534
0.8182 Intermediate Similarity NPC477986
0.8145 Intermediate Similarity NPC477985
0.8145 Intermediate Similarity NPC326386
0.8145 Intermediate Similarity NPC471087
0.8095 Intermediate Similarity NPC173173
0.7969 Intermediate Similarity NPC477988
0.7967 Intermediate Similarity NPC11379
0.7953 Intermediate Similarity NPC471086
0.7795 Intermediate Similarity NPC477987
0.7795 Intermediate Similarity NPC329401
0.7132 Intermediate Similarity NPC230849
0.7109 Intermediate Similarity NPC174463
0.704 Intermediate Similarity NPC58281
0.6977 Remote Similarity NPC284656
0.6942 Remote Similarity NPC473289
0.6846 Remote Similarity NPC235625
0.6694 Remote Similarity NPC75523
0.6691 Remote Similarity NPC133089
0.6667 Remote Similarity NPC130124
0.6667 Remote Similarity NPC193471
0.6591 Remote Similarity NPC201889
0.6591 Remote Similarity NPC106791
0.6589 Remote Similarity NPC474995
0.6555 Remote Similarity NPC471483
0.6555 Remote Similarity NPC469998
0.6538 Remote Similarity NPC475988
0.65 Remote Similarity NPC120335
0.6489 Remote Similarity NPC474984
0.6444 Remote Similarity NPC23963
0.6439 Remote Similarity NPC30196
0.6429 Remote Similarity NPC215507
0.6429 Remote Similarity NPC64168
0.6429 Remote Similarity NPC307165
0.6406 Remote Similarity NPC287572
0.6406 Remote Similarity NPC471636
0.6391 Remote Similarity NPC6531
0.6385 Remote Similarity NPC316984
0.6385 Remote Similarity NPC30911
0.6385 Remote Similarity NPC181510
0.6385 Remote Similarity NPC168758
0.6385 Remote Similarity NPC47857
0.6378 Remote Similarity NPC93179
0.635 Remote Similarity NPC316133
0.635 Remote Similarity NPC318445
0.6349 Remote Similarity NPC80439
0.6349 Remote Similarity NPC173690
0.6349 Remote Similarity NPC6271
0.6349 Remote Similarity NPC279833
0.6336 Remote Similarity NPC60432
0.6336 Remote Similarity NPC1111
0.6336 Remote Similarity NPC261750
0.6336 Remote Similarity NPC279383
0.6331 Remote Similarity NPC314282
0.6328 Remote Similarity NPC250187
0.6328 Remote Similarity NPC271562
0.6299 Remote Similarity NPC44514
0.6299 Remote Similarity NPC477001
0.6299 Remote Similarity NPC469604
0.6299 Remote Similarity NPC477000
0.629 Remote Similarity NPC270813
0.6279 Remote Similarity NPC476034
0.6279 Remote Similarity NPC474969
0.626 Remote Similarity NPC29501
0.626 Remote Similarity NPC473333
0.625 Remote Similarity NPC135216
0.625 Remote Similarity NPC101106
0.6232 Remote Similarity NPC314629
0.6231 Remote Similarity NPC474891
0.6214 Remote Similarity NPC476951
0.6212 Remote Similarity NPC273215
0.6212 Remote Similarity NPC295444
0.6212 Remote Similarity NPC268327
0.621 Remote Similarity NPC2666
0.6198 Remote Similarity NPC299808
0.6198 Remote Similarity NPC118844
0.6198 Remote Similarity NPC110875
0.6198 Remote Similarity NPC72183
0.6194 Remote Similarity NPC477554
0.6187 Remote Similarity NPC314451
0.6187 Remote Similarity NPC314512
0.6187 Remote Similarity NPC313342
0.6187 Remote Similarity NPC313333
0.6183 Remote Similarity NPC127578
0.6179 Remote Similarity NPC150041
0.6179 Remote Similarity NPC471492
0.616 Remote Similarity NPC203627
0.6154 Remote Similarity NPC316401
0.6148 Remote Similarity NPC477553
0.6142 Remote Similarity NPC474244
0.6138 Remote Similarity NPC471256
0.6127 Remote Similarity NPC316205
0.6127 Remote Similarity NPC315387
0.6124 Remote Similarity NPC471844
0.6116 Remote Similarity NPC471184
0.6103 Remote Similarity NPC477555
0.6096 Remote Similarity NPC297058
0.608 Remote Similarity NPC471490
0.608 Remote Similarity NPC476344
0.608 Remote Similarity NPC52820
0.6069 Remote Similarity NPC120420
0.6066 Remote Similarity NPC470520
0.6061 Remote Similarity NPC469603
0.6047 Remote Similarity NPC133420
0.6028 Remote Similarity NPC474371
0.6027 Remote Similarity NPC99864
0.6016 Remote Similarity NPC473520
0.6015 Remote Similarity NPC470534
0.6 Remote Similarity NPC239961
0.6 Remote Similarity NPC288350
0.6 Remote Similarity NPC173329
0.6 Remote Similarity NPC315783
0.6 Remote Similarity NPC82251
0.6 Remote Similarity NPC106446
0.5985 Remote Similarity NPC476956
0.5984 Remote Similarity NPC3436
0.5972 Remote Similarity NPC478139
0.597 Remote Similarity NPC76660
0.597 Remote Similarity NPC469466
0.597 Remote Similarity NPC276995
0.5968 Remote Similarity NPC470521
0.5946 Remote Similarity NPC230889
0.5942 Remote Similarity NPC477515
0.5942 Remote Similarity NPC67917
0.5942 Remote Similarity NPC313802
0.5942 Remote Similarity NPC314268
0.594 Remote Similarity NPC470532
0.594 Remote Similarity NPC470533
0.594 Remote Similarity NPC470527
0.594 Remote Similarity NPC470529
0.594 Remote Similarity NPC470530
0.594 Remote Similarity NPC470531
0.594 Remote Similarity NPC113012
0.594 Remote Similarity NPC470528
0.594 Remote Similarity NPC122926
0.5938 Remote Similarity NPC474873
0.5938 Remote Similarity NPC198992
0.5929 Remote Similarity NPC287236
0.5923 Remote Similarity NPC205176
0.5923 Remote Similarity NPC474917
0.5917 Remote Similarity NPC130436
0.5917 Remote Similarity NPC469861
0.5917 Remote Similarity NPC469860
0.5909 Remote Similarity NPC474099
0.5909 Remote Similarity NPC475960
0.5906 Remote Similarity NPC472015
0.5903 Remote Similarity NPC470539
0.5902 Remote Similarity NPC225283
0.5891 Remote Similarity NPC121423
0.5887 Remote Similarity NPC156553
0.5887 Remote Similarity NPC59646
0.5887 Remote Similarity NPC471255
0.5887 Remote Similarity NPC189651
0.5887 Remote Similarity NPC472195
0.5887 Remote Similarity NPC238090
0.5887 Remote Similarity NPC475098
0.5887 Remote Similarity NPC472196
0.5878 Remote Similarity NPC475918
0.5878 Remote Similarity NPC85670
0.5873 Remote Similarity NPC471843
0.5873 Remote Similarity NPC98165
0.587 Remote Similarity NPC476952
0.5868 Remote Similarity NPC316138
0.5868 Remote Similarity NPC313658
0.5865 Remote Similarity NPC133625
0.5857 Remote Similarity NPC476504
0.5854 Remote Similarity NPC202886
0.5846 Remote Similarity NPC474828
0.5846 Remote Similarity NPC474827
0.5846 Remote Similarity NPC68001
0.5846 Remote Similarity NPC199831
0.5846 Remote Similarity NPC265094
0.584 Remote Similarity NPC256368
0.584 Remote Similarity NPC159698
0.5833 Remote Similarity NPC477793
0.5833 Remote Similarity NPC471494
0.5833 Remote Similarity NPC329919
0.5833 Remote Similarity NPC475074
0.5814 Remote Similarity NPC219038
0.5806 Remote Similarity NPC175842
0.5806 Remote Similarity NPC32494
0.5806 Remote Similarity NPC477749
0.5804 Remote Similarity NPC471263
0.5804 Remote Similarity NPC309525
0.5785 Remote Similarity NPC311163
0.5782 Remote Similarity NPC69496
0.5781 Remote Similarity NPC187268
0.5772 Remote Similarity NPC477748
0.5772 Remote Similarity NPC233910
0.5772 Remote Similarity NPC245836
0.5769 Remote Similarity NPC471599

  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 NPC470000 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
0.6641 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6519 Remote Similarity NPD8080 Discontinued
0.6466 Remote Similarity NPD7641 Discontinued
0.6444 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6385 Remote Similarity NPD2204 Approved
0.6377 Remote Similarity NPD8451 Approved
0.635 Remote Similarity NPD7642 Approved
0.6331 Remote Similarity NPD8448 Approved
0.6312 Remote Similarity NPD8392 Approved
0.6312 Remote Similarity NPD8391 Approved
0.6312 Remote Similarity NPD8390 Approved
0.625 Remote Similarity NPD4211 Phase 1
0.6187 Remote Similarity NPD8299 Approved
0.6187 Remote Similarity NPD8342 Approved
0.6187 Remote Similarity NPD8340 Approved
0.6187 Remote Similarity NPD8341 Approved
0.6143 Remote Similarity NPD8273 Phase 1
0.6096 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6045 Remote Similarity NPD1376 Discontinued
0.6027 Remote Similarity NPD8415 Approved
0.6 Remote Similarity NPD7830 Approved
0.6 Remote Similarity NPD7829 Approved
0.6 Remote Similarity NPD6845 Suspended
0.5983 Remote Similarity NPD882 Phase 2
0.5983 Remote Similarity NPD883 Phase 2
0.5906 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5857 Remote Similarity NPD8444 Approved
0.5833 Remote Similarity NPD8337 Approved
0.5833 Remote Similarity NPD8336 Approved
0.5827 Remote Similarity NPD2495 Phase 3
0.5789 Remote Similarity NPD8384 Approved
0.5782 Remote Similarity NPD2613 Approved
0.5772 Remote Similarity NPD2574 Discontinued
0.5772 Remote Similarity NPD2570 Approved
0.5772 Remote Similarity NPD3615 Approved
0.5772 Remote Similarity NPD2571 Approved
0.5772 Remote Similarity NPD3090 Approved
0.5772 Remote Similarity NPD3088 Approved
0.5772 Remote Similarity NPD2573 Approved
0.5772 Remote Similarity NPD3614 Approved
0.5772 Remote Similarity NPD2566 Approved
0.5772 Remote Similarity NPD3089 Approved
0.5772 Remote Similarity NPD2572 Clinical (unspecified phase)
0.5772 Remote Similarity NPD3087 Approved
0.5772 Remote Similarity NPD4746 Phase 3
0.5772 Remote Similarity NPD3616 Approved
0.5772 Remote Similarity NPD4745 Approved
0.5745 Remote Similarity NPD8268 Approved
0.5745 Remote Similarity NPD8266 Approved
0.5745 Remote Similarity NPD8269 Approved
0.5745 Remote Similarity NPD8267 Approved
0.5714 Remote Similarity NPD8140 Approved
0.5705 Remote Similarity NPD2575 Approved
0.5695 Remote Similarity NPD4684 Phase 3
0.5695 Remote Similarity NPD4685 Phase 3
0.5695 Remote Similarity NPD4686 Approved
0.5676 Remote Similarity NPD8338 Approved
0.5672 Remote Similarity NPD6686 Approved
0.5655 Remote Similarity NPD8074 Phase 3
0.5608 Remote Similarity NPD7260 Phase 2
0.5606 Remote Similarity NPD1407 Approved
0.5606 Remote Similarity NPD8276 Approved
0.5606 Remote Similarity NPD8275 Approved
0.56 Remote Similarity NPD6698 Approved
0.56 Remote Similarity NPD7838 Discovery
0.56 Remote Similarity NPD46 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