Structure

Physi-Chem Properties

Molecular Weight:  361.19
Volume:  364.652
LogP:  0.471
LogD:  1.729
LogS:  -2.645
# Rotatable Bonds:  4
TPSA:  84.86
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.581
Synthetic Accessibility Score:  4.868
Fsp3:  0.7
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:  -5.27
MDCK Permeability:  7.318697316804901e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.148
Human Intestinal Absorption (HIA):  0.03
20% Bioavailability (F20%):  0.033
30% Bioavailability (F30%):  0.172

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.605
Plasma Protein Binding (PPB):  47.66181564331055%
Volume Distribution (VD):  0.551
Pgp-substrate:  68.81103515625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.063
CYP1A2-substrate:  0.034
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.238
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.047
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.193
CYP3A4-inhibitor:  0.271
CYP3A4-substrate:  0.246

ADMET: Excretion

Clearance (CL):  7.234
Half-life (T1/2):  0.768

ADMET: Toxicity

hERG Blockers:  0.442
Human Hepatotoxicity (H-HT):  0.894
Drug-inuced Liver Injury (DILI):  0.197
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.486
Maximum Recommended Daily Dose:  0.974
Skin Sensitization:  0.257
Carcinogencity:  0.131
Eye Corrosion:  0.006
Eye Irritation:  0.013
Respiratory Toxicity:  0.948

Download Data

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

  Natural Product: NPC469466

Natural Product ID:  NPC469466
Common Name*:   Scorzoaustriacin
IUPAC Name:   (3R,3aS,6aR,8S,9aR,9bS)-8-hydroxy-6,9-dimethylidene-3-[[(5-oxooxolan-2-yl)methylamino]methyl]-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
Synonyms:   Scorzoaustriacin
Standard InCHIKey:  VJLHQOFHYPUZLL-QRIARFFBSA-N
Standard InCHI:  InChI=1S/C20H27NO5/c1-10-3-5-13-15(9-21-8-12-4-6-17(23)25-12)20(24)26-19(13)18-11(2)16(22)7-14(10)18/h12-16,18-19,21-22H,1-9H2/t12?,13-,14-,15-,16-,18-,19-/m0/s1
SMILES:  O=C1CCC(O1)CNC[C@@H]1C(=O)O[C@H]2[C@H]1CCC(=C)[C@H]1[C@@H]2C(=C)[C@H](C1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1079457
PubChem CID:   46183621
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO33209 scorzonera austriaca Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[20148526]

☑ 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
NPT111 Cell Line K562 Homo sapiens IC50 = 11300.0 nM PMID[528298]

☑ 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 NPC469466 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
0.9048 High Similarity NPC236644
0.8899 High Similarity NPC76660
0.8899 High Similarity NPC276995
0.8584 High Similarity NPC209734
0.8165 Intermediate Similarity NPC265094
0.8036 Intermediate Similarity NPC15413
0.8017 Intermediate Similarity NPC474371
0.7143 Intermediate Similarity NPC128246
0.713 Intermediate Similarity NPC203170
0.7115 Intermediate Similarity NPC126248
0.708 Intermediate Similarity NPC57976
0.6972 Remote Similarity NPC207114
0.6972 Remote Similarity NPC217983
0.6944 Remote Similarity NPC187661
0.6916 Remote Similarity NPC224386
0.6916 Remote Similarity NPC194859
0.6909 Remote Similarity NPC38392
0.6891 Remote Similarity NPC271562
0.6847 Remote Similarity NPC19087
0.6846 Remote Similarity NPC476951
0.6822 Remote Similarity NPC111409
0.6786 Remote Similarity NPC184063
0.6786 Remote Similarity NPC475925
0.6772 Remote Similarity NPC230849
0.6746 Remote Similarity NPC476952
0.6726 Remote Similarity NPC475788
0.6696 Remote Similarity NPC471843
0.6696 Remote Similarity NPC297474
0.6696 Remote Similarity NPC54065
0.6693 Remote Similarity NPC35037
0.6667 Remote Similarity NPC471844
0.6641 Remote Similarity NPC11379
0.6637 Remote Similarity NPC293001
0.6637 Remote Similarity NPC171360
0.6637 Remote Similarity NPC29821
0.6637 Remote Similarity NPC63193
0.6637 Remote Similarity NPC35959
0.6637 Remote Similarity NPC133888
0.6637 Remote Similarity NPC57304
0.6617 Remote Similarity NPC470539
0.6607 Remote Similarity NPC155935
0.6607 Remote Similarity NPC215556
0.6574 Remote Similarity NPC246076
0.6557 Remote Similarity NPC70235
0.6552 Remote Similarity NPC474297
0.6549 Remote Similarity NPC35809
0.6549 Remote Similarity NPC216284
0.6542 Remote Similarity NPC258965
0.6542 Remote Similarity NPC156658
0.6518 Remote Similarity NPC79549
0.6512 Remote Similarity NPC88190
0.6496 Remote Similarity NPC474313
0.6496 Remote Similarity NPC476344
0.6486 Remote Similarity NPC56593
0.6484 Remote Similarity NPC174463
0.6484 Remote Similarity NPC235625
0.6466 Remote Similarity NPC476053
0.6466 Remote Similarity NPC472873
0.6466 Remote Similarity NPC150041
0.6435 Remote Similarity NPC258216
0.6429 Remote Similarity NPC118601
0.641 Remote Similarity NPC91771
0.641 Remote Similarity NPC24956
0.641 Remote Similarity NPC18019
0.641 Remote Similarity NPC142529
0.6396 Remote Similarity NPC300082
0.6396 Remote Similarity NPC284534
0.6396 Remote Similarity NPC204105
0.6389 Remote Similarity NPC51507
0.6379 Remote Similarity NPC198853
0.6379 Remote Similarity NPC473331
0.6372 Remote Similarity NPC178875
0.6356 Remote Similarity NPC471150
0.6356 Remote Similarity NPC304445
0.6356 Remote Similarity NPC236580
0.635 Remote Similarity NPC133089
0.6348 Remote Similarity NPC155215
0.6339 Remote Similarity NPC304558
0.6339 Remote Similarity NPC64153
0.6333 Remote Similarity NPC67296
0.6325 Remote Similarity NPC213698
0.6325 Remote Similarity NPC170120
0.6325 Remote Similarity NPC163228
0.6303 Remote Similarity NPC249171
0.6303 Remote Similarity NPC49833
0.6296 Remote Similarity NPC173173
0.6293 Remote Similarity NPC200237
0.6283 Remote Similarity NPC475773
0.6283 Remote Similarity NPC24728
0.6281 Remote Similarity NPC80144
0.6281 Remote Similarity NPC86077
0.6269 Remote Similarity NPC309525
0.625 Remote Similarity NPC90476
0.625 Remote Similarity NPC69374
0.6239 Remote Similarity NPC470010
0.6239 Remote Similarity NPC127019
0.6239 Remote Similarity NPC262133
0.6239 Remote Similarity NPC323008
0.6239 Remote Similarity NPC470013
0.623 Remote Similarity NPC215988
0.6228 Remote Similarity NPC471149
0.6222 Remote Similarity NPC317654
0.6222 Remote Similarity NPC96010
0.6222 Remote Similarity NPC470537
0.6222 Remote Similarity NPC280903
0.6218 Remote Similarity NPC311904
0.6218 Remote Similarity NPC263674
0.6218 Remote Similarity NPC181151
0.6218 Remote Similarity NPC261372
0.6218 Remote Similarity NPC58267
0.6218 Remote Similarity NPC161493
0.6212 Remote Similarity NPC23963
0.6212 Remote Similarity NPC476504
0.6207 Remote Similarity NPC133698
0.6207 Remote Similarity NPC131209
0.6204 Remote Similarity NPC478139
0.6204 Remote Similarity NPC477988
0.6202 Remote Similarity NPC471845
0.6202 Remote Similarity NPC241294
0.6202 Remote Similarity NPC471846
0.6202 Remote Similarity NPC202722
0.6202 Remote Similarity NPC39041
0.6198 Remote Similarity NPC171759
0.6198 Remote Similarity NPC150923
0.6195 Remote Similarity NPC470242
0.6195 Remote Similarity NPC309757
0.6195 Remote Similarity NPC236692
0.6194 Remote Similarity NPC477985
0.6194 Remote Similarity NPC326386
0.6194 Remote Similarity NPC471087
0.6186 Remote Similarity NPC67584
0.6186 Remote Similarity NPC52044
0.6186 Remote Similarity NPC304886
0.6176 Remote Similarity NPC471086
0.6174 Remote Similarity NPC283409
0.6174 Remote Similarity NPC472872
0.6154 Remote Similarity NPC153590
0.6154 Remote Similarity NPC60386
0.6154 Remote Similarity NPC473263
0.6154 Remote Similarity NPC473273
0.6154 Remote Similarity NPC308656
0.6154 Remote Similarity NPC473234
0.6154 Remote Similarity NPC65045
0.6142 Remote Similarity NPC470534
0.614 Remote Similarity NPC186148
0.6134 Remote Similarity NPC213078
0.6129 Remote Similarity NPC195841
0.6129 Remote Similarity NPC233256
0.6119 Remote Similarity NPC477990
0.6119 Remote Similarity NPC323168
0.6119 Remote Similarity NPC477989
0.6119 Remote Similarity NPC111162
0.6119 Remote Similarity NPC293550
0.6116 Remote Similarity NPC186861
0.6116 Remote Similarity NPC471381
0.6107 Remote Similarity NPC471109
0.6102 Remote Similarity NPC477131
0.6098 Remote Similarity NPC473148
0.6094 Remote Similarity NPC23967
0.609 Remote Similarity NPC238323
0.6087 Remote Similarity NPC58219
0.6087 Remote Similarity NPC307165
0.6087 Remote Similarity NPC177629
0.6087 Remote Similarity NPC91248
0.6087 Remote Similarity NPC215507
0.6074 Remote Similarity NPC476503
0.6074 Remote Similarity NPC469999
0.6071 Remote Similarity NPC245665
0.6068 Remote Similarity NPC286341
0.6068 Remote Similarity NPC191339
0.6066 Remote Similarity NPC474348
0.6066 Remote Similarity NPC188785
0.6063 Remote Similarity NPC473232
0.6058 Remote Similarity NPC478136
0.6058 Remote Similarity NPC5714
0.6053 Remote Similarity NPC162071
0.6053 Remote Similarity NPC67493
0.605 Remote Similarity NPC40663
0.6047 Remote Similarity NPC193471
0.6047 Remote Similarity NPC130124
0.6043 Remote Similarity NPC120335
0.6034 Remote Similarity NPC92974
0.6034 Remote Similarity NPC12872
0.6034 Remote Similarity NPC168679
0.6033 Remote Similarity NPC45125
0.6033 Remote Similarity NPC221615
0.6017 Remote Similarity NPC472874
0.6017 Remote Similarity NPC469998
0.6017 Remote Similarity NPC135776
0.6 Remote Similarity NPC44004
0.6 Remote Similarity NPC190753
0.6 Remote Similarity NPC475217
0.6 Remote Similarity NPC471380
0.6 Remote Similarity NPC54737
0.6 Remote Similarity NPC237540
0.6 Remote Similarity NPC270270
0.5985 Remote Similarity NPC106791
0.5985 Remote Similarity NPC201889
0.5984 Remote Similarity NPC70865
0.5983 Remote Similarity NPC37607

  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 NPC469466 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
0.6462 Remote Similarity NPD8266 Approved
0.6462 Remote Similarity NPD8267 Approved
0.6462 Remote Similarity NPD8268 Approved
0.6462 Remote Similarity NPD8269 Approved
0.5938 Remote Similarity NPD6420 Discontinued
0.5913 Remote Similarity NPD4249 Approved
0.5909 Remote Similarity NPD617 Approved
0.5891 Remote Similarity NPD2204 Approved
0.5882 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5862 Remote Similarity NPD4250 Approved
0.5862 Remote Similarity NPD4251 Approved
0.5789 Remote Similarity NPD5362 Discontinued
0.5778 Remote Similarity NPD8347 Approved
0.5778 Remote Similarity NPD8345 Approved
0.5778 Remote Similarity NPD8346 Approved
0.5766 Remote Similarity NPD7122 Discontinued
0.5763 Remote Similarity NPD1695 Approved
0.5725 Remote Similarity NPD8340 Approved
0.5725 Remote Similarity NPD8342 Approved
0.5725 Remote Similarity NPD8341 Approved
0.5725 Remote Similarity NPD8299 Approved
0.5704 Remote Similarity NPD2101 Approved
0.5704 Remote Similarity NPD7518 Approved
0.5704 Remote Similarity NPD7517 Approved
0.5704 Remote Similarity NPD7519 Approved
0.5703 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5692 Remote Similarity NPD8087 Discontinued
0.5692 Remote Similarity NPD6421 Discontinued
0.5691 Remote Similarity NPD3713 Approved
0.5691 Remote Similarity NPD3715 Approved
0.5691 Remote Similarity NPD3714 Approved
0.5683 Remote Similarity NPD8273 Phase 1
0.5672 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5662 Remote Similarity NPD7148 Clinical (unspecified phase)
0.5662 Remote Similarity NPD7147 Phase 3
0.563 Remote Similarity NPD7641 Discontinued
0.5614 Remote Similarity NPD4790 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