Structure

Physi-Chem Properties

Molecular Weight:  363.17
Volume:  350.227
LogP:  1.502
LogD:  1.532
LogS:  -1.342
# Rotatable Bonds:  2
TPSA:  84.12
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.642
Synthetic Accessibility Score:  6.062
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:  -5.562
MDCK Permeability:  6.96371789672412e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.895
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.22
Plasma Protein Binding (PPB):  62.1581916809082%
Volume Distribution (VD):  2.224
Pgp-substrate:  41.043907165527344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.228
CYP1A2-substrate:  0.892
CYP2C19-inhibitor:  0.037
CYP2C19-substrate:  0.632
CYP2C9-inhibitor:  0.018
CYP2C9-substrate:  0.118
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.328
CYP3A4-inhibitor:  0.061
CYP3A4-substrate:  0.619

ADMET: Excretion

Clearance (CL):  13.181
Half-life (T1/2):  0.946

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.547
Drug-inuced Liver Injury (DILI):  0.16
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.94
Maximum Recommended Daily Dose:  0.805
Skin Sensitization:  0.312
Carcinogencity:  0.489
Eye Corrosion:  0.003
Eye Irritation:  0.02
Respiratory Toxicity:  0.803

Download Data

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

  Natural Product: NPC469997

Natural Product ID:  NPC469997
Common Name*:   Stemocurtisine N-Oxide
IUPAC Name:   n.a.
Synonyms:   Stemocurtisine N-Oxide
Standard InCHIKey:  NBMMUYZDDIKEKL-KMUTXKEPSA-N
Standard InCHI:  InChI=1S/C19H25NO6/c1-10-13-14-12-6-4-8-20(14,22)9-5-7-19(13,25-12)26-16(10)17-15(23-3)11(2)18(21)24-17/h10,12-14H,4-9H2,1-3H3/b17-16-/t10-,12-,13+,14-,19+,20?/m0/s1
SMILES:  CC1C2C3C4CCC[N+]3(CCCC2(O4)OC1=C5C(=C(C(=O)O5)C)OC)[O-]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1641983
PubChem CID:   53323085
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. root n.a. PMID[21049906]
NPO1235 Stemona curtisii Species Stemonaceae Eukaryota n.a. n.a. 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 = 500.0 ng PMID[452716]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens MIC = 1.38 nM PMID[452716]

☑ 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 NPC469997 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 NPC470000
0.9626 High Similarity NPC43648
0.9279 High Similarity NPC65045
0.8729 High Similarity NPC469999
0.8462 Intermediate Similarity NPC138534
0.8462 Intermediate Similarity NPC477986
0.8361 Intermediate Similarity NPC173173
0.8182 Intermediate Similarity NPC323168
0.8182 Intermediate Similarity NPC477990
0.8182 Intermediate Similarity NPC293550
0.8182 Intermediate Similarity NPC477989
0.8182 Intermediate Similarity NPC111162
0.8049 Intermediate Similarity NPC477987
0.8049 Intermediate Similarity NPC329401
0.7823 Intermediate Similarity NPC471087
0.7823 Intermediate Similarity NPC326386
0.7823 Intermediate Similarity NPC477985
0.7795 Intermediate Similarity NPC477988
0.7642 Intermediate Similarity NPC11379
0.7638 Intermediate Similarity NPC471086
0.736 Intermediate Similarity NPC230849
0.7339 Intermediate Similarity NPC174463
0.7273 Intermediate Similarity NPC58281
0.6917 Remote Similarity NPC75523
0.6797 Remote Similarity NPC284656
0.6783 Remote Similarity NPC469998
0.6618 Remote Similarity NPC215507
0.6618 Remote Similarity NPC307165
0.6612 Remote Similarity NPC473289
0.6585 Remote Similarity NPC93179
0.6538 Remote Similarity NPC235625
0.6522 Remote Similarity NPC133089
0.6504 Remote Similarity NPC44514
0.65 Remote Similarity NPC270813
0.6484 Remote Similarity NPC130124
0.6484 Remote Similarity NPC193471
0.641 Remote Similarity NPC118844
0.641 Remote Similarity NPC110875
0.641 Remote Similarity NPC299808
0.641 Remote Similarity NPC72183
0.6357 Remote Similarity NPC475988
0.6308 Remote Similarity NPC474984
0.6288 Remote Similarity NPC201889
0.6288 Remote Similarity NPC106791
0.6279 Remote Similarity NPC474995
0.627 Remote Similarity NPC250187
0.6269 Remote Similarity NPC23963
0.624 Remote Similarity NPC133420
0.622 Remote Similarity NPC476034
0.622 Remote Similarity NPC287572
0.622 Remote Similarity NPC471636
0.622 Remote Similarity NPC474969
0.6218 Remote Similarity NPC471483
0.6214 Remote Similarity NPC120335
0.6202 Remote Similarity NPC168758
0.6202 Remote Similarity NPC47857
0.6202 Remote Similarity NPC181510
0.6202 Remote Similarity NPC316984
0.6202 Remote Similarity NPC30911
0.6142 Remote Similarity NPC271562
0.6136 Remote Similarity NPC30196
0.6136 Remote Similarity NPC477554
0.6124 Remote Similarity NPC470532
0.6124 Remote Similarity NPC470528
0.6124 Remote Similarity NPC470529
0.6124 Remote Similarity NPC470533
0.6124 Remote Similarity NPC470530
0.6124 Remote Similarity NPC470531
0.6124 Remote Similarity NPC470527
0.6121 Remote Similarity NPC469860
0.6121 Remote Similarity NPC130436
0.6121 Remote Similarity NPC469861
0.6111 Remote Similarity NPC64168
0.6111 Remote Similarity NPC469604
0.609 Remote Similarity NPC477553
0.609 Remote Similarity NPC6531
0.6066 Remote Similarity NPC471843
0.6063 Remote Similarity NPC135216
0.6063 Remote Similarity NPC101106
0.6058 Remote Similarity NPC316133
0.6058 Remote Similarity NPC318445
0.6045 Remote Similarity NPC477555
0.6043 Remote Similarity NPC314282
0.6032 Remote Similarity NPC279833
0.6032 Remote Similarity NPC80439
0.6032 Remote Similarity NPC173690
0.6032 Remote Similarity NPC6271
0.6031 Remote Similarity NPC60432
0.6031 Remote Similarity NPC261750
0.6031 Remote Similarity NPC279383
0.6031 Remote Similarity NPC1111
0.6 Remote Similarity NPC127578
0.5984 Remote Similarity NPC477000
0.5984 Remote Similarity NPC471492
0.5984 Remote Similarity NPC150041
0.5984 Remote Similarity NPC477001
0.5954 Remote Similarity NPC29501
0.5952 Remote Similarity NPC474244
0.5942 Remote Similarity NPC314629
0.5938 Remote Similarity NPC471844
0.5935 Remote Similarity NPC473333
0.5929 Remote Similarity NPC476951
0.5923 Remote Similarity NPC474891
0.5917 Remote Similarity NPC471184
0.5909 Remote Similarity NPC273215
0.5909 Remote Similarity NPC295444
0.5909 Remote Similarity NPC268327
0.5899 Remote Similarity NPC313342
0.5899 Remote Similarity NPC321197
0.5899 Remote Similarity NPC314451
0.5899 Remote Similarity NPC314512
0.5899 Remote Similarity NPC313333
0.5887 Remote Similarity NPC471490
0.5887 Remote Similarity NPC476344
0.5887 Remote Similarity NPC2666
0.5887 Remote Similarity NPC52820
0.5878 Remote Similarity NPC469603
0.5874 Remote Similarity NPC316401
0.5862 Remote Similarity NPC471256
0.5845 Remote Similarity NPC315387
0.5845 Remote Similarity NPC316205
0.584 Remote Similarity NPC203627
0.5833 Remote Similarity NPC470534
0.5833 Remote Similarity NPC242877
0.5833 Remote Similarity NPC64913
0.5822 Remote Similarity NPC297058
0.5793 Remote Similarity NPC120420
0.5775 Remote Similarity NPC478136
0.576 Remote Similarity NPC153559
0.5753 Remote Similarity NPC99864
0.5745 Remote Similarity NPC474371
0.5738 Remote Similarity NPC470520
0.5736 Remote Similarity NPC307846
0.5736 Remote Similarity NPC305157
0.5736 Remote Similarity NPC205176
0.5734 Remote Similarity NPC470539
0.5726 Remote Similarity NPC170286
0.5725 Remote Similarity NPC474099
0.5725 Remote Similarity NPC470535
0.5714 Remote Similarity NPC124181
0.5714 Remote Similarity NPC315783
0.5714 Remote Similarity NPC473307
0.5704 Remote Similarity NPC106446
0.5694 Remote Similarity NPC478139
0.5693 Remote Similarity NPC476956
0.5692 Remote Similarity NPC239961
0.5692 Remote Similarity NPC82251
0.5691 Remote Similarity NPC473520
0.5682 Remote Similarity NPC470536
0.568 Remote Similarity NPC288350
0.568 Remote Similarity NPC173329
0.5676 Remote Similarity NPC230889
0.5672 Remote Similarity NPC276995
0.5672 Remote Similarity NPC76660
0.5672 Remote Similarity NPC469466
0.5669 Remote Similarity NPC469402
0.5669 Remote Similarity NPC26597
0.5659 Remote Similarity NPC68001
0.5659 Remote Similarity NPC474828
0.5659 Remote Similarity NPC199831
0.5659 Remote Similarity NPC265094
0.5659 Remote Similarity NPC474827
0.5656 Remote Similarity NPC80875
0.5656 Remote Similarity NPC3436
0.5656 Remote Similarity NPC159568
0.5652 Remote Similarity NPC313802
0.5652 Remote Similarity NPC67917
0.5652 Remote Similarity NPC477515
0.5652 Remote Similarity NPC314268
0.5645 Remote Similarity NPC470521
0.5643 Remote Similarity NPC287236
0.5639 Remote Similarity NPC122926
0.5639 Remote Similarity NPC113012
0.5635 Remote Similarity NPC472167
0.5635 Remote Similarity NPC241426
0.5625 Remote Similarity NPC198992
0.5625 Remote Similarity NPC474873
0.5625 Remote Similarity NPC470994
0.5625 Remote Similarity NPC474348
0.5625 Remote Similarity NPC219038
0.5615 Remote Similarity NPC474917
0.5612 Remote Similarity NPC147635
0.5612 Remote Similarity NPC163693
0.561 Remote Similarity NPC175842
0.561 Remote Similarity NPC32494
0.5606 Remote Similarity NPC475960
0.5603 Remote Similarity NPC471255
0.56 Remote Similarity NPC241407
0.56 Remote Similarity NPC291709

  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 NPC469997 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
0.6336 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6222 Remote Similarity NPD8080 Discontinued
0.6202 Remote Similarity NPD2204 Approved
0.6165 Remote Similarity NPD7641 Discontinued
0.6148 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6087 Remote Similarity NPD8451 Approved
0.6063 Remote Similarity NPD4211 Phase 1
0.6058 Remote Similarity NPD7642 Approved
0.6043 Remote Similarity NPD8448 Approved
0.6028 Remote Similarity NPD8392 Approved
0.6028 Remote Similarity NPD8390 Approved
0.6028 Remote Similarity NPD8391 Approved
0.6 Remote Similarity NPD8336 Approved
0.6 Remote Similarity NPD8337 Approved
0.5899 Remote Similarity NPD8299 Approved
0.5899 Remote Similarity NPD8342 Approved
0.5899 Remote Similarity NPD8340 Approved
0.5899 Remote Similarity NPD8341 Approved
0.5857 Remote Similarity NPD8273 Phase 1
0.5833 Remote Similarity NPD6845 Suspended
0.5833 Remote Similarity NPD8338 Approved
0.5822 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5753 Remote Similarity NPD8415 Approved
0.5746 Remote Similarity NPD1376 Discontinued
0.5714 Remote Similarity NPD7830 Approved
0.5714 Remote Similarity NPD7829 Approved
0.5641 Remote Similarity NPD882 Phase 2
0.5641 Remote Similarity NPD883 Phase 2

  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