Structure

Physi-Chem Properties

Molecular Weight:  361.15
Volume:  347.59
LogP:  1.489
LogD:  2.12
LogS:  -2.865
# Rotatable Bonds:  2
TPSA:  81.37
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.872
Synthetic Accessibility Score:  5.483
Fsp3:  0.632
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:  -4.931
MDCK Permeability:  1.8163424101658165e-05
Pgp-inhibitor:  0.04
Pgp-substrate:  0.187
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.172
30% Bioavailability (F30%):  0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.507
Plasma Protein Binding (PPB):  80.92574310302734%
Volume Distribution (VD):  1.226
Pgp-substrate:  23.224834442138672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.123
CYP1A2-substrate:  0.856
CYP2C19-inhibitor:  0.068
CYP2C19-substrate:  0.636
CYP2C9-inhibitor:  0.075
CYP2C9-substrate:  0.101
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.212
CYP3A4-inhibitor:  0.172
CYP3A4-substrate:  0.392

ADMET: Excretion

Clearance (CL):  10.115
Half-life (T1/2):  0.498

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.857
Drug-inuced Liver Injury (DILI):  0.715
AMES Toxicity:  0.025
Rat Oral Acute Toxicity:  0.89
Maximum Recommended Daily Dose:  0.335
Skin Sensitization:  0.43
Carcinogencity:  0.661
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.046

Download Data

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

  Natural Product: NPC469999

Natural Product ID:  NPC469999
Common Name*:   GGFNFNQWBNJLAV-ZYBONQNOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  GGFNFNQWBNJLAV-ZYBONQNOSA-N
Standard InCHI:  InChI=1S/C19H23NO6/c1-9-13-14-11-5-6-12(21)20(14)8-4-7-19(13,25-11)26-16(9)17-15(23-3)10(2)18(22)24-17/h9,11,13-14H,4-8H2,1-3H3/b17-16-/t9-,11-,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)CCC(=O)N1CCC2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1642206
PubChem CID:   53323980
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 = 500.0 ng PMID[490686]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens MIC = 2.11 nM PMID[490686]

☑ 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 NPC469999 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
0.9035 High Similarity NPC43648
0.8934 High Similarity NPC173173
0.8729 High Similarity NPC469997
0.8729 High Similarity NPC65045
0.8443 Intermediate Similarity NPC470000
0.8211 Intermediate Similarity NPC11379
0.8 Intermediate Similarity NPC58281
0.7984 Intermediate Similarity NPC138534
0.7984 Intermediate Similarity NPC477986
0.792 Intermediate Similarity NPC230849
0.7903 Intermediate Similarity NPC174463
0.7734 Intermediate Similarity NPC111162
0.7734 Intermediate Similarity NPC323168
0.7734 Intermediate Similarity NPC477989
0.7734 Intermediate Similarity NPC293550
0.7734 Intermediate Similarity NPC477990
0.7615 Intermediate Similarity NPC329401
0.7615 Intermediate Similarity NPC477987
0.7405 Intermediate Similarity NPC471087
0.7405 Intermediate Similarity NPC477985
0.7405 Intermediate Similarity NPC326386
0.7388 Intermediate Similarity NPC477988
0.7239 Intermediate Similarity NPC471086
0.7132 Intermediate Similarity NPC215507
0.7094 Intermediate Similarity NPC469998
0.7007 Intermediate Similarity NPC307165
0.6957 Remote Similarity NPC120335
0.6906 Remote Similarity NPC133089
0.6639 Remote Similarity NPC471843
0.6567 Remote Similarity NPC235625
0.6562 Remote Similarity NPC271562
0.6538 Remote Similarity NPC469603
0.6522 Remote Similarity NPC321197
0.6515 Remote Similarity NPC193471
0.6515 Remote Similarity NPC130124
0.6484 Remote Similarity NPC471844
0.6466 Remote Similarity NPC474984
0.6423 Remote Similarity NPC23963
0.6412 Remote Similarity NPC470527
0.6412 Remote Similarity NPC470528
0.6412 Remote Similarity NPC470531
0.6412 Remote Similarity NPC470529
0.6412 Remote Similarity NPC470530
0.6412 Remote Similarity NPC470532
0.6412 Remote Similarity NPC470533
0.6406 Remote Similarity NPC133420
0.6389 Remote Similarity NPC120420
0.6385 Remote Similarity NPC474099
0.6345 Remote Similarity NPC99864
0.6331 Remote Similarity NPC318445
0.6331 Remote Similarity NPC316133
0.6328 Remote Similarity NPC199831
0.6328 Remote Similarity NPC474827
0.6328 Remote Similarity NPC474828
0.6328 Remote Similarity NPC68001
0.6324 Remote Similarity NPC284656
0.6324 Remote Similarity NPC201889
0.6324 Remote Similarity NPC106791
0.6316 Remote Similarity NPC474995
0.6312 Remote Similarity NPC476951
0.6312 Remote Similarity NPC314282
0.6296 Remote Similarity NPC30196
0.629 Remote Similarity NPC150041
0.6279 Remote Similarity NPC469604
0.6279 Remote Similarity NPC75523
0.625 Remote Similarity NPC473289
0.625 Remote Similarity NPC6531
0.6242 Remote Similarity NPC475342
0.6241 Remote Similarity NPC168758
0.6241 Remote Similarity NPC181510
0.6241 Remote Similarity NPC316984
0.6241 Remote Similarity NPC30911
0.6241 Remote Similarity NPC47857
0.6241 Remote Similarity NPC309525
0.6231 Remote Similarity NPC93179
0.623 Remote Similarity NPC159568
0.6224 Remote Similarity NPC470539
0.6214 Remote Similarity NPC314629
0.6194 Remote Similarity NPC60432
0.6194 Remote Similarity NPC261750
0.6194 Remote Similarity NPC1111
0.619 Remote Similarity NPC476344
0.617 Remote Similarity NPC314451
0.617 Remote Similarity NPC313333
0.617 Remote Similarity NPC313342
0.617 Remote Similarity NPC314512
0.6167 Remote Similarity NPC130436
0.6167 Remote Similarity NPC469861
0.6167 Remote Similarity NPC469860
0.6154 Remote Similarity NPC44514
0.6138 Remote Similarity NPC316401
0.6127 Remote Similarity NPC474371
0.6124 Remote Similarity NPC474244
0.6119 Remote Similarity NPC470534
0.6111 Remote Similarity NPC316205
0.6111 Remote Similarity NPC315387
0.6094 Remote Similarity NPC26597
0.6077 Remote Similarity NPC265094
0.6074 Remote Similarity NPC469466
0.6063 Remote Similarity NPC52820
0.6048 Remote Similarity NPC118844
0.6048 Remote Similarity NPC299808
0.6048 Remote Similarity NPC72183
0.6048 Remote Similarity NPC110875
0.6045 Remote Similarity NPC63511
0.6031 Remote Similarity NPC307846
0.6031 Remote Similarity NPC305157
0.6029 Remote Similarity NPC475988
0.6029 Remote Similarity NPC469597
0.6015 Remote Similarity NPC470535
0.6 Remote Similarity NPC194750
0.6 Remote Similarity NPC287638
0.6 Remote Similarity NPC233274
0.5973 Remote Similarity NPC82129
0.5971 Remote Similarity NPC476952
0.597 Remote Similarity NPC470536
0.5968 Remote Similarity NPC80875
0.5959 Remote Similarity NPC478139
0.5956 Remote Similarity NPC76660
0.5956 Remote Similarity NPC314550
0.5956 Remote Similarity NPC276995
0.5948 Remote Similarity NPC71866
0.5942 Remote Similarity NPC470538
0.594 Remote Similarity NPC250187
0.5933 Remote Similarity NPC230889
0.5931 Remote Similarity NPC478136
0.5926 Remote Similarity NPC127578
0.5923 Remote Similarity NPC188785
0.5923 Remote Similarity NPC474348
0.5918 Remote Similarity NPC315011
0.5915 Remote Similarity NPC287236
0.5909 Remote Similarity NPC474917
0.5909 Remote Similarity NPC64168
0.5909 Remote Similarity NPC87919
0.5909 Remote Similarity NPC205176
0.5906 Remote Similarity NPC471256
0.5896 Remote Similarity NPC476034
0.5896 Remote Similarity NPC474969
0.5896 Remote Similarity NPC287572
0.5896 Remote Similarity NPC475960
0.5896 Remote Similarity NPC471636
0.5891 Remote Similarity NPC270813
0.5887 Remote Similarity NPC147635
0.5887 Remote Similarity NPC88190
0.5887 Remote Similarity NPC163693
0.5882 Remote Similarity NPC474411
0.5882 Remote Similarity NPC474431
0.5874 Remote Similarity NPC315783
0.5873 Remote Similarity NPC471483
0.5873 Remote Similarity NPC473520
0.5862 Remote Similarity NPC280903
0.5859 Remote Similarity NPC301596
0.5859 Remote Similarity NPC172998
0.5859 Remote Similarity NPC299396
0.5857 Remote Similarity NPC471109
0.5857 Remote Similarity NPC476956
0.5847 Remote Similarity NPC216090
0.5846 Remote Similarity NPC469402
0.5844 Remote Similarity NPC304299
0.5844 Remote Similarity NPC475278
0.5844 Remote Similarity NPC309450
0.5844 Remote Similarity NPC247776
0.5844 Remote Similarity NPC475266
0.5839 Remote Similarity NPC475987
0.5839 Remote Similarity NPC313348
0.5833 Remote Similarity NPC80439
0.5833 Remote Similarity NPC173690
0.5833 Remote Similarity NPC279833
0.5833 Remote Similarity NPC6271
0.5827 Remote Similarity NPC477554
0.5817 Remote Similarity NPC315210
0.5817 Remote Similarity NPC315848
0.5816 Remote Similarity NPC313802
0.5816 Remote Similarity NPC477515
0.5816 Remote Similarity NPC314268
0.5816 Remote Similarity NPC67917
0.5814 Remote Similarity NPC241426
0.5804 Remote Similarity NPC273185
0.5786 Remote Similarity NPC475642
0.5786 Remote Similarity NPC477553
0.5785 Remote Similarity NPC170286
0.5781 Remote Similarity NPC273197
0.5781 Remote Similarity NPC234339
0.5781 Remote Similarity NPC167893
0.5781 Remote Similarity NPC224689
0.5775 Remote Similarity NPC477140
0.5775 Remote Similarity NPC477143
0.5769 Remote Similarity NPC279561
0.5769 Remote Similarity NPC472015
0.5769 Remote Similarity NPC203627
0.5769 Remote Similarity NPC187268
0.5758 Remote Similarity NPC86077
0.5753 Remote Similarity NPC470537
0.5748 Remote Similarity NPC473723
0.5748 Remote Similarity NPC473663
0.5748 Remote Similarity NPC475173
0.5748 Remote Similarity NPC473561
0.5746 Remote Similarity NPC135216
0.5746 Remote Similarity NPC469401
0.5746 Remote Similarity NPC101106

  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 NPC469999 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
0.6493 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6444 Remote Similarity NPD7641 Discontinued
0.6414 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6391 Remote Similarity NPD1376 Discontinued
0.6377 Remote Similarity NPD8080 Discontinued
0.6357 Remote Similarity NPD8451 Approved
0.6357 Remote Similarity NPD8273 Phase 1
0.6345 Remote Similarity NPD8415 Approved
0.6331 Remote Similarity NPD7642 Approved
0.6312 Remote Similarity NPD8448 Approved
0.6304 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6294 Remote Similarity NPD8391 Approved
0.6294 Remote Similarity NPD8390 Approved
0.6294 Remote Similarity NPD8392 Approved
0.6241 Remote Similarity NPD2204 Approved
0.617 Remote Similarity NPD8299 Approved
0.617 Remote Similarity NPD8340 Approved
0.617 Remote Similarity NPD8342 Approved
0.617 Remote Similarity NPD8341 Approved
0.6154 Remote Similarity NPD8336 Approved
0.6154 Remote Similarity NPD8337 Approved
0.6096 Remote Similarity NPD6845 Suspended
0.6093 Remote Similarity NPD8384 Approved
0.5986 Remote Similarity NPD8338 Approved
0.5918 Remote Similarity NPD2101 Approved
0.5874 Remote Similarity NPD7829 Approved
0.5874 Remote Similarity NPD7830 Approved
0.5859 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5816 Remote Similarity NPD2495 Phase 3
0.5802 Remote Similarity NPD8414 Discontinued
0.5746 Remote Similarity NPD4211 Phase 1
0.5734 Remote Similarity NPD8267 Approved
0.5734 Remote Similarity NPD8269 Approved
0.5734 Remote Similarity NPD8444 Approved
0.5734 Remote Similarity NPD8268 Approved
0.5734 Remote Similarity NPD8266 Approved
0.5705 Remote Similarity NPD7260 Phase 2
0.5704 Remote Similarity NPD2132 Phase 3
0.5674 Remote Similarity NPD961 Discontinued
0.5667 Remote Similarity NPD2613 Approved
0.5658 Remote Similarity NPD2573 Approved
0.5658 Remote Similarity NPD3087 Approved
0.5658 Remote Similarity NPD3615 Approved
0.5658 Remote Similarity NPD2570 Approved
0.5658 Remote Similarity NPD2571 Approved
0.5658 Remote Similarity NPD2574 Discontinued
0.5658 Remote Similarity NPD3088 Approved
0.5658 Remote Similarity NPD4746 Phase 3
0.5658 Remote Similarity NPD2572 Clinical (unspecified phase)
0.5658 Remote Similarity NPD3614 Approved
0.5658 Remote Similarity NPD3089 Approved
0.5658 Remote Similarity NPD3090 Approved
0.5658 Remote Similarity NPD4745 Approved
0.5658 Remote Similarity NPD2566 Approved
0.5658 Remote Similarity NPD3616 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