Structure

Physi-Chem Properties

Molecular Weight:  511.22
Volume:  516.209
LogP:  3.032
LogD:  0.799
LogS:  -3.129
# Rotatable Bonds:  4
TPSA:  147.4
# H-Bond Aceptor:  9
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.25
Synthetic Accessibility Score:  6.032
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.489
MDCK Permeability:  1.5476693079108372e-05
Pgp-inhibitor:  0.467
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.029
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.543
Plasma Protein Binding (PPB):  83.03417205810547%
Volume Distribution (VD):  0.947
Pgp-substrate:  9.218077659606934%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.448
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.686
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.006
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.032
CYP3A4-inhibitor:  0.449
CYP3A4-substrate:  0.922

ADMET: Excretion

Clearance (CL):  5.837
Half-life (T1/2):  0.096

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.142
Drug-inuced Liver Injury (DILI):  0.956
AMES Toxicity:  0.025
Rat Oral Acute Toxicity:  0.997
Maximum Recommended Daily Dose:  0.956
Skin Sensitization:  0.683
Carcinogencity:  0.74
Eye Corrosion:  0.017
Eye Irritation:  0.03
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC201899

Natural Product ID:  NPC201899
Common Name*:   FBUMTPMBZLYMGG-XNLMCKFUSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  FBUMTPMBZLYMGG-XNLMCKFUSA-N
Standard InCHI:  InChI=1S/C28H33NO8/c1-7-9-10-12-16(30)18-20(32)14(3)23(33)26(5)21(18)25(4)24(34)19-17(31)13-15(11-8-2)29-22(19)27(6,35)28(25,36)37-26/h7-12,15,21,29-30,33,35-36H,13H2,1-6H3/b9-7+,11-8+,12-10+,18-16+/t15-,21+,25+,26-,27-,28+/m0/s1
SMILES:  C/C=C/C=C/C(=C1/C(=O)C(=C([C@]2(C)[C@H]1[C@]1(C)C(=O)C3=C([C@@](C)([C@]1(O)O2)O)N[C@@H](/C=C/C)CC3=O)O)C)/O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3093410
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003487] Cyclic ketones
              • [CHEMONTID:0000125] Quinomethanes
                • [CHEMONTID:0002122] O-quinomethanes

*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
NPO32579 Penicillium sp. F23-2 Strain Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24215398]
NPO32579 Penicillium sp. F23-2 Strain Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26540093]

☑ 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
NPT168 Cell Line P388 Mus musculus IC50 > 10000.0 nM PMID[570526]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 10000.0 nM PMID[570526]
NPT71 Cell Line HEK293 Homo sapiens IC50 > 10000.0 nM PMID[570526]
NPT165 Cell Line HeLa Homo sapiens IC50 > 10000.0 nM PMID[570526]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[570526]

☑ 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 NPC201899 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
1.0 High Similarity NPC471674
0.8667 High Similarity NPC110294
0.8252 Intermediate Similarity NPC471672
0.6667 Remote Similarity NPC96010
0.6667 Remote Similarity NPC317654
0.6599 Remote Similarity NPC477140
0.6599 Remote Similarity NPC477143
0.6575 Remote Similarity NPC471673
0.6513 Remote Similarity NPC478136
0.6447 Remote Similarity NPC204556
0.6429 Remote Similarity NPC478139
0.6408 Remote Similarity NPC168883
0.6395 Remote Similarity NPC476190
0.6389 Remote Similarity NPC38159
0.6364 Remote Similarity NPC300026
0.6358 Remote Similarity NPC315783
0.6346 Remote Similarity NPC314361
0.634 Remote Similarity NPC314282
0.634 Remote Similarity NPC473249
0.6329 Remote Similarity NPC297058
0.6316 Remote Similarity NPC314451
0.6316 Remote Similarity NPC314512
0.6316 Remote Similarity NPC313333
0.6316 Remote Similarity NPC313342
0.6309 Remote Similarity NPC477515
0.6309 Remote Similarity NPC313802
0.6309 Remote Similarity NPC314268
0.6309 Remote Similarity NPC35037
0.6309 Remote Similarity NPC67917
0.6284 Remote Similarity NPC6531
0.6284 Remote Similarity NPC316325
0.6282 Remote Similarity NPC316401
0.6276 Remote Similarity NPC324683
0.6266 Remote Similarity NPC99864
0.6258 Remote Similarity NPC315387
0.6258 Remote Similarity NPC316205
0.625 Remote Similarity NPC318445
0.625 Remote Similarity NPC314629
0.625 Remote Similarity NPC316133
0.6242 Remote Similarity NPC168879
0.6242 Remote Similarity NPC284707
0.6229 Remote Similarity NPC473040
0.6225 Remote Similarity NPC315915
0.6216 Remote Similarity NPC30196
0.6209 Remote Similarity NPC470922
0.6209 Remote Similarity NPC476729
0.6203 Remote Similarity NPC120420
0.6197 Remote Similarity NPC133420
0.619 Remote Similarity NPC471204
0.6184 Remote Similarity NPC478138
0.6184 Remote Similarity NPC269642
0.6182 Remote Similarity NPC316249
0.6181 Remote Similarity NPC220730
0.6178 Remote Similarity NPC102316
0.6174 Remote Similarity NPC469684
0.6174 Remote Similarity NPC53396
0.6174 Remote Similarity NPC98249
0.617 Remote Similarity NPC235369
0.6169 Remote Similarity NPC181999
0.6164 Remote Similarity NPC188738
0.6159 Remote Similarity NPC93271
0.6159 Remote Similarity NPC135576
0.6159 Remote Similarity NPC476815
0.6159 Remote Similarity NPC473145
0.6149 Remote Similarity NPC247069
0.6144 Remote Similarity NPC265557
0.6144 Remote Similarity NPC105926
0.6144 Remote Similarity NPC91693
0.6144 Remote Similarity NPC67251
0.6144 Remote Similarity NPC18945
0.6122 Remote Similarity NPC60432
0.6122 Remote Similarity NPC269530
0.6122 Remote Similarity NPC476269
0.6118 Remote Similarity NPC23963
0.6118 Remote Similarity NPC475383
0.6118 Remote Similarity NPC187497
0.6118 Remote Similarity NPC156379
0.6118 Remote Similarity NPC113620
0.6118 Remote Similarity NPC100612
0.6118 Remote Similarity NPC475599
0.6118 Remote Similarity NPC174336
0.6115 Remote Similarity NPC239895
0.6104 Remote Similarity NPC24651
0.6101 Remote Similarity NPC242486
0.6101 Remote Similarity NPC15215
0.6099 Remote Similarity NPC244456
0.6099 Remote Similarity NPC9878
0.6099 Remote Similarity NPC469657
0.6096 Remote Similarity NPC286880
0.6093 Remote Similarity NPC245320
0.6087 Remote Similarity NPC230889
0.6081 Remote Similarity NPC469463
0.6081 Remote Similarity NPC469496
0.6081 Remote Similarity NPC469454
0.6078 Remote Similarity NPC312833
0.6071 Remote Similarity NPC80738
0.6069 Remote Similarity NPC24596
0.6067 Remote Similarity NPC473968
0.6067 Remote Similarity NPC475642
0.6067 Remote Similarity NPC23046
0.6065 Remote Similarity NPC473635
0.6065 Remote Similarity NPC293112
0.6065 Remote Similarity NPC225049
0.6059 Remote Similarity NPC265699
0.6059 Remote Similarity NPC475527
0.6059 Remote Similarity NPC314050
0.6059 Remote Similarity NPC315809
0.6054 Remote Similarity NPC247031
0.6054 Remote Similarity NPC304180
0.6054 Remote Similarity NPC179798
0.6054 Remote Similarity NPC132790
0.6054 Remote Similarity NPC97939
0.6054 Remote Similarity NPC100329
0.6053 Remote Similarity NPC31641
0.604 Remote Similarity NPC474181
0.6039 Remote Similarity NPC469789
0.6038 Remote Similarity NPC476111
0.6026 Remote Similarity NPC478205
0.6026 Remote Similarity NPC108581
0.6026 Remote Similarity NPC201889
0.6026 Remote Similarity NPC296361
0.6026 Remote Similarity NPC476008
0.6026 Remote Similarity NPC475913
0.6026 Remote Similarity NPC9714
0.6026 Remote Similarity NPC106791
0.6026 Remote Similarity NPC478206
0.6026 Remote Similarity NPC476951
0.6025 Remote Similarity NPC251998
0.6025 Remote Similarity NPC243014
0.6014 Remote Similarity NPC205534
0.6014 Remote Similarity NPC25666
0.6014 Remote Similarity NPC261750
0.6014 Remote Similarity NPC236217
0.6014 Remote Similarity NPC469819
0.6014 Remote Similarity NPC1111
0.6014 Remote Similarity NPC271059
0.6014 Remote Similarity NPC114162
0.6013 Remote Similarity NPC46570
0.6013 Remote Similarity NPC201359
0.6013 Remote Similarity NPC170880
0.6 Remote Similarity NPC28280
0.6 Remote Similarity NPC478216
0.6 Remote Similarity NPC8369
0.6 Remote Similarity NPC304646
0.6 Remote Similarity NPC81736
0.6 Remote Similarity NPC64318
0.6 Remote Similarity NPC318135
0.6 Remote Similarity NPC172154
0.6 Remote Similarity NPC27105
0.6 Remote Similarity NPC803
0.6 Remote Similarity NPC176840
0.5988 Remote Similarity NPC45813
0.5988 Remote Similarity NPC596
0.5988 Remote Similarity NPC140045
0.5988 Remote Similarity NPC295885
0.5987 Remote Similarity NPC475834
0.5987 Remote Similarity NPC475041
0.5987 Remote Similarity NPC305260
0.5987 Remote Similarity NPC476529
0.5987 Remote Similarity NPC241050
0.5987 Remote Similarity NPC245094
0.5987 Remote Similarity NPC470186
0.5987 Remote Similarity NPC475775
0.5987 Remote Similarity NPC474179
0.5987 Remote Similarity NPC268958
0.5987 Remote Similarity NPC270850
0.5986 Remote Similarity NPC473627
0.5986 Remote Similarity NPC37116
0.5986 Remote Similarity NPC34193
0.5986 Remote Similarity NPC478211
0.5986 Remote Similarity NPC476290
0.5976 Remote Similarity NPC315210
0.5976 Remote Similarity NPC315848
0.5975 Remote Similarity NPC90814
0.5975 Remote Similarity NPC189393
0.5974 Remote Similarity NPC23786
0.5974 Remote Similarity NPC470265
0.5974 Remote Similarity NPC107493
0.5974 Remote Similarity NPC287236
0.5974 Remote Similarity NPC170538
0.5973 Remote Similarity NPC25909
0.5973 Remote Similarity NPC56448
0.5973 Remote Similarity NPC478212
0.5973 Remote Similarity NPC475966
0.5973 Remote Similarity NPC193471
0.5973 Remote Similarity NPC130124
0.5972 Remote Similarity NPC472756
0.5965 Remote Similarity NPC12124
0.5965 Remote Similarity NPC44200
0.5963 Remote Similarity NPC262813
0.5962 Remote Similarity NPC477745
0.596 Remote Similarity NPC271621
0.596 Remote Similarity NPC477116
0.596 Remote Similarity NPC478204
0.596 Remote Similarity NPC59751
0.596 Remote Similarity NPC27999
0.596 Remote Similarity NPC27413
0.5959 Remote Similarity NPC473807
0.5959 Remote Similarity NPC151393
0.5957 Remote Similarity NPC177680

  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 NPC201899 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
0.6933 Remote Similarity NPD7260 Phase 2
0.6776 Remote Similarity NPD6845 Suspended
0.6622 Remote Similarity NPD7624 Clinical (unspecified phase)
0.6622 Remote Similarity NPD7623 Phase 3
0.6554 Remote Similarity NPD8444 Approved
0.6554 Remote Similarity NPD7739 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6914 Discontinued
0.6382 Remote Similarity NPD8451 Approved
0.6358 Remote Similarity NPD7829 Approved
0.6358 Remote Similarity NPD7830 Approved
0.634 Remote Similarity NPD7747 Phase 1
0.634 Remote Similarity NPD7746 Phase 1
0.634 Remote Similarity NPD8448 Approved
0.6323 Remote Similarity NPD8390 Approved
0.6323 Remote Similarity NPD8391 Approved
0.6323 Remote Similarity NPD8392 Approved
0.6316 Remote Similarity NPD8342 Approved
0.6316 Remote Similarity NPD8340 Approved
0.6316 Remote Similarity NPD8299 Approved
0.6316 Remote Similarity NPD8341 Approved
0.6284 Remote Similarity NPD7500 Approved
0.6266 Remote Similarity NPD8415 Approved
0.625 Remote Similarity NPD7642 Approved
0.6226 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6159 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6133 Remote Similarity NPD7641 Discontinued
0.6129 Remote Similarity NPD8074 Phase 3
0.6054 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6013 Remote Similarity NPD6921 Approved
0.6013 Remote Similarity NPD8513 Phase 3
0.5974 Remote Similarity NPD8080 Discontinued
0.596 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5909 Remote Similarity NPD8515 Approved
0.5909 Remote Similarity NPD8517 Approved
0.5909 Remote Similarity NPD8516 Approved
0.5909 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5886 Remote Similarity NPD8336 Approved
0.5886 Remote Similarity NPD8337 Approved
0.586 Remote Similarity NPD8273 Phase 1
0.5851 Remote Similarity NPD8407 Phase 2
0.5839 Remote Similarity NPD2204 Approved
0.5839 Remote Similarity NPD8338 Approved
0.5812 Remote Similarity NPD8360 Approved
0.5812 Remote Similarity NPD8361 Approved
0.5806 Remote Similarity NPD8266 Approved
0.5806 Remote Similarity NPD8268 Approved
0.5806 Remote Similarity NPD8267 Approved
0.5806 Remote Similarity NPD8269 Approved
0.5752 Remote Similarity NPD7115 Discovery
0.5729 Remote Similarity NPD8435 Approved
0.5723 Remote Similarity NPD8389 Clinical (unspecified phase)
0.5691 Remote Similarity NPD8368 Discontinued
0.5655 Remote Similarity NPD8384 Approved
0.5625 Remote Similarity NPD8424 Clinical (unspecified phase)

  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