Structure

Physi-Chem Properties

Molecular Weight:  405.22
Volume:  402.115
LogP:  2.844
LogD:  3.36
LogS:  -3.788
# Rotatable Bonds:  4
TPSA:  84.53
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.796
Synthetic Accessibility Score:  5.91
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:  -4.892
MDCK Permeability:  4.254570376360789e-05
Pgp-inhibitor:  0.133
Pgp-substrate:  0.882
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.057
30% Bioavailability (F30%):  0.8

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.732
Plasma Protein Binding (PPB):  75.55292510986328%
Volume Distribution (VD):  3.218
Pgp-substrate:  22.84046173095703%

ADMET: Metabolism

CYP1A2-inhibitor:  0.113
CYP1A2-substrate:  0.257
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.838
CYP2C9-inhibitor:  0.036
CYP2C9-substrate:  0.116
CYP2D6-inhibitor:  0.197
CYP2D6-substrate:  0.73
CYP3A4-inhibitor:  0.092
CYP3A4-substrate:  0.822

ADMET: Excretion

Clearance (CL):  12.862
Half-life (T1/2):  0.393

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.552
Drug-inuced Liver Injury (DILI):  0.665
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.822
Maximum Recommended Daily Dose:  0.163
Skin Sensitization:  0.405
Carcinogencity:  0.174
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.936

Download Data

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

  Natural Product: NPC65045

Natural Product ID:  NPC65045
Common Name*:   Stemocurtisinol
IUPAC Name:   n.a.
Synonyms:   Stemocurtisinol
Standard InCHIKey:  WAULTDWQPCNZBI-YJXDLYNPSA-N
Standard InCHI:  InChI=1S/C22H31NO6/c1-5-14(24)13-7-8-15-17-16-11(2)19(20-18(26-4)12(3)21(25)27-20)29-22(16,28-15)9-6-10-23(13)17/h11,13-17,24H,5-10H2,1-4H3/b20-19-/t11-,13-,14-,15-,16+,17-,22+/m0/s1
SMILES:  CC[C@@H]([C@@H]1CC[C@H]2[C@H]3[C@H]4[C@H](C)/C(=C/5C(=C(C)C(=O)O5)OC)/O[C@@]4(CCCN13)O2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL467414
PubChem CID:   44566734
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. 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. rhizome 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[544204]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens MIC = 2.47 nM PMID[544204]
NPT4944 Organism Anopheles minimus Anopheles minimus LC50 = 39.0 ppm PMID[544203]

☑ 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 NPC65045 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 NPC469997
0.8803 High Similarity NPC111162
0.8803 High Similarity NPC323168
0.8803 High Similarity NPC477990
0.8803 High Similarity NPC293550
0.8803 High Similarity NPC477989
0.8729 High Similarity NPC469999
0.8462 Intermediate Similarity NPC477986
0.8462 Intermediate Similarity NPC138534
0.8417 Intermediate Similarity NPC471087
0.8417 Intermediate Similarity NPC326386
0.8417 Intermediate Similarity NPC477985
0.8361 Intermediate Similarity NPC173173
0.8235 Intermediate Similarity NPC11379
0.8226 Intermediate Similarity NPC477988
0.8211 Intermediate Similarity NPC471086
0.8049 Intermediate Similarity NPC329401
0.8049 Intermediate Similarity NPC477987
0.736 Intermediate Similarity NPC230849
0.7339 Intermediate Similarity NPC174463
0.7273 Intermediate Similarity NPC58281
0.7179 Intermediate Similarity NPC473289
0.7063 Intermediate Similarity NPC235625
0.6889 Remote Similarity NPC133089
0.688 Remote Similarity NPC193471
0.688 Remote Similarity NPC130124
0.68 Remote Similarity NPC474995
0.6797 Remote Similarity NPC106791
0.6797 Remote Similarity NPC201889
0.6783 Remote Similarity NPC469998
0.6783 Remote Similarity NPC471483
0.6746 Remote Similarity NPC475988
0.6693 Remote Similarity NPC474984
0.6691 Remote Similarity NPC120335
0.6667 Remote Similarity NPC284656
0.6641 Remote Similarity NPC23963
0.6641 Remote Similarity NPC30196
0.6639 Remote Similarity NPC64168
0.6639 Remote Similarity NPC75523
0.6618 Remote Similarity NPC215507
0.6618 Remote Similarity NPC307165
0.6613 Remote Similarity NPC287572
0.6613 Remote Similarity NPC471636
0.6589 Remote Similarity NPC6531
0.6587 Remote Similarity NPC47857
0.6587 Remote Similarity NPC316984
0.6587 Remote Similarity NPC30911
0.6587 Remote Similarity NPC168758
0.6587 Remote Similarity NPC181510
0.6585 Remote Similarity NPC93179
0.6557 Remote Similarity NPC6271
0.6557 Remote Similarity NPC173690
0.6557 Remote Similarity NPC80439
0.6557 Remote Similarity NPC279833
0.6541 Remote Similarity NPC318445
0.6541 Remote Similarity NPC316133
0.6535 Remote Similarity NPC261750
0.6535 Remote Similarity NPC60432
0.6535 Remote Similarity NPC1111
0.6535 Remote Similarity NPC279383
0.6532 Remote Similarity NPC271562
0.6532 Remote Similarity NPC250187
0.6519 Remote Similarity NPC314282
0.6504 Remote Similarity NPC477000
0.6504 Remote Similarity NPC44514
0.6504 Remote Similarity NPC477001
0.6504 Remote Similarity NPC469604
0.648 Remote Similarity NPC474969
0.648 Remote Similarity NPC476034
0.6471 Remote Similarity NPC473333
0.6457 Remote Similarity NPC29501
0.6452 Remote Similarity NPC135216
0.6452 Remote Similarity NPC101106
0.6429 Remote Similarity NPC474891
0.6418 Remote Similarity NPC314629
0.6417 Remote Similarity NPC2666
0.641 Remote Similarity NPC299808
0.641 Remote Similarity NPC118844
0.641 Remote Similarity NPC110875
0.641 Remote Similarity NPC72183
0.6406 Remote Similarity NPC268327
0.6406 Remote Similarity NPC273215
0.6406 Remote Similarity NPC295444
0.6397 Remote Similarity NPC476951
0.6387 Remote Similarity NPC150041
0.6387 Remote Similarity NPC471492
0.6385 Remote Similarity NPC477554
0.6378 Remote Similarity NPC127578
0.637 Remote Similarity NPC314451
0.637 Remote Similarity NPC313342
0.637 Remote Similarity NPC314512
0.637 Remote Similarity NPC313333
0.6364 Remote Similarity NPC203627
0.6341 Remote Similarity NPC474244
0.6336 Remote Similarity NPC477553
0.6331 Remote Similarity NPC316401
0.6325 Remote Similarity NPC471184
0.632 Remote Similarity NPC471844
0.6312 Remote Similarity NPC471256
0.6304 Remote Similarity NPC315387
0.6304 Remote Similarity NPC316205
0.6288 Remote Similarity NPC477555
0.6281 Remote Similarity NPC471490
0.6281 Remote Similarity NPC52820
0.6281 Remote Similarity NPC476344
0.6271 Remote Similarity NPC470520
0.6268 Remote Similarity NPC297058
0.625 Remote Similarity NPC469603
0.6241 Remote Similarity NPC120420
0.624 Remote Similarity NPC133420
0.623 Remote Similarity NPC270813
0.6218 Remote Similarity NPC473520
0.6204 Remote Similarity NPC474371
0.6202 Remote Similarity NPC470534
0.6198 Remote Similarity NPC173329
0.6198 Remote Similarity NPC288350
0.6197 Remote Similarity NPC99864
0.619 Remote Similarity NPC82251
0.619 Remote Similarity NPC239961
0.6186 Remote Similarity NPC3436
0.6183 Remote Similarity NPC106446
0.6176 Remote Similarity NPC315783
0.6167 Remote Similarity NPC470521
0.6165 Remote Similarity NPC476956
0.6154 Remote Similarity NPC469466
0.6154 Remote Similarity NPC276995
0.6154 Remote Similarity NPC76660
0.6143 Remote Similarity NPC478139
0.6129 Remote Similarity NPC474873
0.6129 Remote Similarity NPC198992
0.6124 Remote Similarity NPC122926
0.6124 Remote Similarity NPC470530
0.6124 Remote Similarity NPC470531
0.6124 Remote Similarity NPC470528
0.6124 Remote Similarity NPC470533
0.6124 Remote Similarity NPC470532
0.6124 Remote Similarity NPC470527
0.6124 Remote Similarity NPC113012
0.6124 Remote Similarity NPC470529
0.6121 Remote Similarity NPC469860
0.6121 Remote Similarity NPC469861
0.6121 Remote Similarity NPC130436
0.6119 Remote Similarity NPC477515
0.6119 Remote Similarity NPC313802
0.6119 Remote Similarity NPC67917
0.6119 Remote Similarity NPC314268
0.6111 Remote Similarity NPC230889
0.6111 Remote Similarity NPC474917
0.6111 Remote Similarity NPC205176
0.6103 Remote Similarity NPC287236
0.6102 Remote Similarity NPC225283
0.6098 Remote Similarity NPC472015
0.6094 Remote Similarity NPC475960
0.6094 Remote Similarity NPC474099
0.6083 Remote Similarity NPC472196
0.6083 Remote Similarity NPC472195
0.6083 Remote Similarity NPC59646
0.6083 Remote Similarity NPC156553
0.6083 Remote Similarity NPC238090
0.6083 Remote Similarity NPC475098
0.6083 Remote Similarity NPC189651
0.608 Remote Similarity NPC121423
0.6071 Remote Similarity NPC470539
0.6068 Remote Similarity NPC313658
0.6068 Remote Similarity NPC316138
0.6066 Remote Similarity NPC471843
0.6066 Remote Similarity NPC98165
0.6063 Remote Similarity NPC85670
0.6063 Remote Similarity NPC475918
0.6058 Remote Similarity NPC471255
0.605 Remote Similarity NPC202886
0.6047 Remote Similarity NPC133625
0.6045 Remote Similarity NPC476952
0.6034 Remote Similarity NPC471494
0.6033 Remote Similarity NPC159698
0.6033 Remote Similarity NPC256368
0.6032 Remote Similarity NPC199831
0.6032 Remote Similarity NPC474828
0.6032 Remote Similarity NPC474827
0.6032 Remote Similarity NPC68001
0.6032 Remote Similarity NPC265094
0.6029 Remote Similarity NPC476504
0.6016 Remote Similarity NPC475074
0.6 Remote Similarity NPC477793
0.6 Remote Similarity NPC175842
0.6 Remote Similarity NPC32494
0.6 Remote Similarity NPC477749
0.6 Remote Similarity NPC329919
0.6 Remote Similarity NPC219038
0.5983 Remote Similarity NPC311163
0.5971 Remote Similarity NPC309525
0.5971 Remote Similarity NPC471263
0.5968 Remote Similarity NPC187268
0.5966 Remote Similarity NPC477748
0.5952 Remote Similarity NPC471599
0.5952 Remote Similarity NPC86077
0.595 Remote Similarity NPC472640
0.595 Remote Similarity NPC475173

  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 NPC65045 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
0.685 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6718 Remote Similarity NPD8080 Discontinued
0.6667 Remote Similarity NPD7641 Discontinued
0.6641 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6587 Remote Similarity NPD2204 Approved
0.6567 Remote Similarity NPD8451 Approved
0.6541 Remote Similarity NPD7642 Approved
0.6519 Remote Similarity NPD8448 Approved
0.6496 Remote Similarity NPD8390 Approved
0.6496 Remote Similarity NPD8392 Approved
0.6496 Remote Similarity NPD8391 Approved
0.6452 Remote Similarity NPD4211 Phase 1
0.637 Remote Similarity NPD8340 Approved
0.637 Remote Similarity NPD8299 Approved
0.637 Remote Similarity NPD8341 Approved
0.637 Remote Similarity NPD8342 Approved
0.6324 Remote Similarity NPD8273 Phase 1
0.6268 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6231 Remote Similarity NPD1376 Discontinued
0.6197 Remote Similarity NPD8415 Approved
0.6195 Remote Similarity NPD883 Phase 2
0.6195 Remote Similarity NPD882 Phase 2
0.6176 Remote Similarity NPD7830 Approved
0.6176 Remote Similarity NPD7829 Approved
0.617 Remote Similarity NPD6845 Suspended
0.6098 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6029 Remote Similarity NPD8444 Approved
0.6 Remote Similarity NPD2495 Phase 3
0.6 Remote Similarity NPD8337 Approved
0.6 Remote Similarity NPD8336 Approved
0.5946 Remote Similarity NPD8384 Approved
0.5944 Remote Similarity NPD2613 Approved
0.5931 Remote Similarity NPD2574 Discontinued
0.5931 Remote Similarity NPD3616 Approved
0.5931 Remote Similarity NPD3615 Approved
0.5931 Remote Similarity NPD3088 Approved
0.5931 Remote Similarity NPD4746 Phase 3
0.5931 Remote Similarity NPD3089 Approved
0.5931 Remote Similarity NPD2573 Approved
0.5931 Remote Similarity NPD3090 Approved
0.5931 Remote Similarity NPD3614 Approved
0.5931 Remote Similarity NPD2571 Approved
0.5931 Remote Similarity NPD3087 Approved
0.5931 Remote Similarity NPD2566 Approved
0.5931 Remote Similarity NPD2570 Approved
0.5931 Remote Similarity NPD2572 Clinical (unspecified phase)
0.5931 Remote Similarity NPD4745 Approved
0.5912 Remote Similarity NPD8267 Approved
0.5912 Remote Similarity NPD8268 Approved
0.5912 Remote Similarity NPD8269 Approved
0.5912 Remote Similarity NPD8266 Approved
0.5891 Remote Similarity NPD8140 Approved
0.5855 Remote Similarity NPD2575 Approved
0.585 Remote Similarity NPD4684 Phase 3
0.585 Remote Similarity NPD4686 Approved
0.585 Remote Similarity NPD4685 Phase 3
0.5846 Remote Similarity NPD6686 Approved
0.5833 Remote Similarity NPD8338 Approved
0.5785 Remote Similarity NPD6698 Approved
0.5785 Remote Similarity NPD46 Approved
0.5785 Remote Similarity NPD7838 Discovery
0.5781 Remote Similarity NPD8276 Approved
0.5781 Remote Similarity NPD1407 Approved
0.5781 Remote Similarity NPD8275 Approved
0.5769 Remote Similarity NPD8307 Discontinued
0.5764 Remote Similarity NPD7260 Phase 2
0.5758 Remote Similarity NPD6421 Discontinued
0.5705 Remote Similarity NPD8389 Clinical (unspecified phase)
0.5703 Remote Similarity NPD8086 Approved
0.5703 Remote Similarity NPD8085 Approved
0.5703 Remote Similarity NPD8082 Approved
0.5703 Remote Similarity NPD8139 Approved
0.5703 Remote Similarity NPD8084 Approved
0.5703 Remote Similarity NPD8083 Approved
0.5703 Remote Similarity NPD8138 Approved
0.5692 Remote Similarity NPD8393 Approved
0.5672 Remote Similarity NPD6429 Approved
0.5672 Remote Similarity NPD6430 Approved
0.566 Remote Similarity NPD8414 Discontinued
0.5655 Remote Similarity NPD2101 Approved
0.5639 Remote Similarity NPD8087 Discontinued
0.562 Remote Similarity NPD7500 Approved
0.562 Remote Similarity NPD7505 Discontinued
0.5615 Remote Similarity NPD8081 Approved
0.5612 Remote Similarity NPD8346 Approved
0.5612 Remote Similarity NPD8347 Approved
0.5612 Remote Similarity NPD8345 Approved
0.5603 Remote Similarity NPD7122 Discontinued

  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