Structure

Physi-Chem Properties

Molecular Weight:  639.3
Volume:  634.465
LogP:  2.338
LogD:  1.91
LogS:  -4.403
# Rotatable Bonds:  6
TPSA:  131.01
# H-Bond Aceptor:  11
# H-Bond Donor:  2
# Rings:  7
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.342
Synthetic Accessibility Score:  6.235
Fsp3:  0.657
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.381
MDCK Permeability:  4.544648254523054e-05
Pgp-inhibitor:  0.993
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.93
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.236
Plasma Protein Binding (PPB):  21.417444229125977%
Volume Distribution (VD):  2.103
Pgp-substrate:  29.78754425048828%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.098
CYP2C19-inhibitor:  0.051
CYP2C19-substrate:  0.099
CYP2C9-inhibitor:  0.095
CYP2C9-substrate:  0.002
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.095
CYP3A4-inhibitor:  0.629
CYP3A4-substrate:  0.345

ADMET: Excretion

Clearance (CL):  1.444
Half-life (T1/2):  0.576

ADMET: Toxicity

hERG Blockers:  0.203
Human Hepatotoxicity (H-HT):  0.856
Drug-inuced Liver Injury (DILI):  0.116
AMES Toxicity:  0.959
Rat Oral Acute Toxicity:  0.245
Maximum Recommended Daily Dose:  0.806
Skin Sensitization:  0.964
Carcinogencity:  0.12
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.958

Download Data

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

  Natural Product: NPC274293

Natural Product ID:  NPC274293
Common Name*:   Tamulamide A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QBNANTHTVCSSKS-PXIDHJHOSA-N
Standard InCHI:  InChI=1S/C35H45NO10/c1-20(38)36-19-31-22(39)15-27-30(43-31)17-34(2)33(44-27)18-35(3)32(46-34)13-12-26-29(45-35)16-28-25(41-26)11-10-23-24(42-28)9-8-21(40-23)7-5-4-6-14-37/h4-14,21-33,39H,15-19H2,1-3H3,(H,36,38)/b6-4+,7-5+/t21-,22-,23+,24-,25-,26+,27+,28+,29-,30-,31+,32-,33-,34+,35+/m1/s1
SMILES:  CC(=NC[C@H]1[C@@H](C[C@H]2[C@@H](C[C@@]3(C)[C@@H](C[C@@]4(C)[C@@H](C=C[C@H]5[C@@H](C[C@H]6[C@@H](C=C[C@H]7[C@@H](C=C[C@@H](/C=C/C=C/C=O)O7)O6)O5)O4)O3)O2)O1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1097208
PubChem CID:   46211326
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0002204] C-glycosyl compounds

*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
NPO19460 Karenia brevis Species Kareniaceae Eukaryota n.a. n.a. n.a. PMID[15679307]
NPO19460 Karenia brevis Species Kareniaceae Eukaryota n.a. n.a. n.a. PMID[20218657]
NPO19460 Karenia brevis Species Kareniaceae 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
NPT3134 Organism Ovis aries Ovis aries Activity = 39.0 % PMID[483022]
NPT3134 Organism Ovis aries Ovis aries Activity = 43.0 % PMID[483022]
NPT3134 Organism Ovis aries Ovis aries Activity = 42.0 % PMID[483022]
NPT3134 Organism Ovis aries Ovis aries Activity = 34.0 % PMID[483022]
NPT2 Others Unspecified Ki = 2500.0 nM PMID[483022]

☑ 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 NPC274293 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 NPC172197
0.7049 Intermediate Similarity NPC29501
0.6957 Remote Similarity NPC175614
0.6897 Remote Similarity NPC475332
0.6777 Remote Similarity NPC315070
0.6723 Remote Similarity NPC475655
0.6723 Remote Similarity NPC2313
0.6723 Remote Similarity NPC471637
0.6723 Remote Similarity NPC57586
0.6723 Remote Similarity NPC475157
0.6723 Remote Similarity NPC154132
0.6639 Remote Similarity NPC154601
0.6612 Remote Similarity NPC197736
0.6609 Remote Similarity NPC476084
0.6609 Remote Similarity NPC476075
0.6567 Remote Similarity NPC68293
0.6567 Remote Similarity NPC262845
0.6471 Remote Similarity NPC475646
0.6466 Remote Similarity NPC471324
0.6466 Remote Similarity NPC206679
0.6466 Remote Similarity NPC114172
0.6457 Remote Similarity NPC469865
0.6444 Remote Similarity NPC314282
0.6443 Remote Similarity NPC475527
0.6443 Remote Similarity NPC265699
0.6438 Remote Similarity NPC244380
0.6438 Remote Similarity NPC61717
0.6429 Remote Similarity NPC122926
0.6429 Remote Similarity NPC113012
0.641 Remote Similarity NPC159092
0.641 Remote Similarity NPC109406
0.64 Remote Similarity NPC113620
0.64 Remote Similarity NPC174336
0.64 Remote Similarity NPC187497
0.64 Remote Similarity NPC475599
0.64 Remote Similarity NPC100612
0.6397 Remote Similarity NPC477793
0.6397 Remote Similarity NPC329919
0.6393 Remote Similarity NPC477198
0.6387 Remote Similarity NPC475503
0.6377 Remote Similarity NPC316401
0.6371 Remote Similarity NPC271269
0.6364 Remote Similarity NPC225978
0.6364 Remote Similarity NPC271207
0.6364 Remote Similarity NPC255175
0.6364 Remote Similarity NPC206711
0.635 Remote Similarity NPC315387
0.635 Remote Similarity NPC316205
0.6349 Remote Similarity NPC133625
0.6349 Remote Similarity NPC473578
0.6345 Remote Similarity NPC284625
0.6345 Remote Similarity NPC69176
0.6343 Remote Similarity NPC16709
0.6333 Remote Similarity NPC120299
0.632 Remote Similarity NPC251330
0.6311 Remote Similarity NPC169365
0.6311 Remote Similarity NPC197447
0.6301 Remote Similarity NPC214821
0.6301 Remote Similarity NPC298067
0.6296 Remote Similarity NPC313333
0.6296 Remote Similarity NPC314512
0.6296 Remote Similarity NPC313342
0.6296 Remote Similarity NPC314451
0.6283 Remote Similarity NPC477199
0.6281 Remote Similarity NPC475653
0.625 Remote Similarity NPC189629
0.625 Remote Similarity NPC477385
0.625 Remote Similarity NPC255410
0.625 Remote Similarity NPC477390
0.6242 Remote Similarity NPC298005
0.6242 Remote Similarity NPC36463
0.6239 Remote Similarity NPC177668
0.6233 Remote Similarity NPC193579
0.6233 Remote Similarity NPC298469
0.6233 Remote Similarity NPC141669
0.6222 Remote Similarity NPC315783
0.6207 Remote Similarity NPC316186
0.6195 Remote Similarity NPC44261
0.6194 Remote Similarity NPC475383
0.6194 Remote Similarity NPC156379
0.6181 Remote Similarity NPC302276
0.6167 Remote Similarity NPC300710
0.6165 Remote Similarity NPC241050
0.616 Remote Similarity NPC75523
0.6154 Remote Similarity NPC133450
0.6148 Remote Similarity NPC469943
0.6142 Remote Similarity NPC193765
0.6142 Remote Similarity NPC475150
0.6136 Remote Similarity NPC475642
0.6129 Remote Similarity NPC473596
0.6124 Remote Similarity NPC297945
0.6124 Remote Similarity NPC126897
0.6121 Remote Similarity NPC199382
0.6119 Remote Similarity NPC477140
0.6119 Remote Similarity NPC477143
0.6116 Remote Similarity NPC197294
0.6116 Remote Similarity NPC45313
0.6116 Remote Similarity NPC8098
0.6116 Remote Similarity NPC288350
0.6116 Remote Similarity NPC183449
0.6116 Remote Similarity NPC173329
0.6103 Remote Similarity NPC314629
0.6102 Remote Similarity NPC3952
0.6096 Remote Similarity NPC162910
0.6083 Remote Similarity NPC256368
0.6083 Remote Similarity NPC282088
0.6083 Remote Similarity NPC54961
0.6083 Remote Similarity NPC158445
0.6083 Remote Similarity NPC156782
0.6083 Remote Similarity NPC157353
0.6077 Remote Similarity NPC478024
0.6077 Remote Similarity NPC241477
0.6077 Remote Similarity NPC279383
0.6069 Remote Similarity NPC180770
0.6058 Remote Similarity NPC469494
0.6058 Remote Similarity NPC204639
0.605 Remote Similarity NPC475603
0.605 Remote Similarity NPC61894
0.6045 Remote Similarity NPC314268
0.6045 Remote Similarity NPC477515
0.6045 Remote Similarity NPC313802
0.6045 Remote Similarity NPC67917
0.6036 Remote Similarity NPC474833
0.6034 Remote Similarity NPC311163
0.6034 Remote Similarity NPC477389
0.6034 Remote Similarity NPC477387
0.6033 Remote Similarity NPC233273
0.6033 Remote Similarity NPC205546
0.6033 Remote Similarity NPC50902
0.6033 Remote Similarity NPC189764
0.6032 Remote Similarity NPC74035
0.6028 Remote Similarity NPC139585
0.6027 Remote Similarity NPC315848
0.6027 Remote Similarity NPC315210
0.6018 Remote Similarity NPC315731
0.6018 Remote Similarity NPC184208
0.6018 Remote Similarity NPC8538
0.6018 Remote Similarity NPC474894
0.6016 Remote Similarity NPC473807
0.6016 Remote Similarity NPC65700
0.6014 Remote Similarity NPC235772
0.6014 Remote Similarity NPC280941
0.6 Remote Similarity NPC473289
0.6 Remote Similarity NPC475098
0.6 Remote Similarity NPC189651
0.6 Remote Similarity NPC71680
0.6 Remote Similarity NPC128501
0.5986 Remote Similarity NPC73829
0.5986 Remote Similarity NPC119794
0.5985 Remote Similarity NPC318445
0.5985 Remote Similarity NPC316133
0.5984 Remote Similarity NPC265502
0.5984 Remote Similarity NPC472433
0.5984 Remote Similarity NPC201128
0.5984 Remote Similarity NPC93026
0.5984 Remote Similarity NPC469960
0.5984 Remote Similarity NPC29389
0.5984 Remote Similarity NPC475918
0.5983 Remote Similarity NPC477388
0.5983 Remote Similarity NPC477386
0.5969 Remote Similarity NPC313668
0.5969 Remote Similarity NPC298484
0.5969 Remote Similarity NPC315836
0.5968 Remote Similarity NPC227865
0.5966 Remote Similarity NPC139782
0.5966 Remote Similarity NPC43074
0.5966 Remote Similarity NPC209047
0.5966 Remote Similarity NPC74672
0.5966 Remote Similarity NPC242503
0.5954 Remote Similarity NPC295444
0.5954 Remote Similarity NPC268327
0.5954 Remote Similarity NPC273215
0.5952 Remote Similarity NPC309398
0.5952 Remote Similarity NPC280566
0.5952 Remote Similarity NPC183570
0.595 Remote Similarity NPC17290
0.595 Remote Similarity NPC35269
0.595 Remote Similarity NPC70323
0.595 Remote Similarity NPC192066
0.595 Remote Similarity NPC256570
0.595 Remote Similarity NPC469491
0.595 Remote Similarity NPC3568
0.595 Remote Similarity NPC23454
0.595 Remote Similarity NPC262312
0.5946 Remote Similarity NPC475152
0.5946 Remote Similarity NPC475394
0.5946 Remote Similarity NPC475584
0.5944 Remote Similarity NPC78189
0.5938 Remote Similarity NPC108682
0.5938 Remote Similarity NPC472263
0.5938 Remote Similarity NPC469959
0.5938 Remote Similarity NPC469957
0.5932 Remote Similarity NPC60765
0.5931 Remote Similarity NPC230889
0.5929 Remote Similarity NPC470147
0.5929 Remote Similarity NPC133226
0.5923 Remote Similarity NPC15551
0.5923 Remote Similarity NPC181298
0.592 Remote Similarity NPC175531
0.5917 Remote Similarity NPC182632

  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 NPC274293 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
0.6544 Remote Similarity NPD8392 Approved
0.6544 Remote Similarity NPD8391 Approved
0.6544 Remote Similarity NPD8390 Approved
0.6493 Remote Similarity NPD8451 Approved
0.6444 Remote Similarity NPD8448 Approved
0.6296 Remote Similarity NPD8340 Approved
0.6296 Remote Similarity NPD8341 Approved
0.6296 Remote Similarity NPD8342 Approved
0.6296 Remote Similarity NPD8299 Approved
0.626 Remote Similarity NPD7505 Discontinued
0.6239 Remote Similarity NPD7838 Discovery
0.6222 Remote Similarity NPD7829 Approved
0.6222 Remote Similarity NPD7830 Approved
0.6172 Remote Similarity NPD6421 Discontinued
0.6148 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6124 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5985 Remote Similarity NPD7642 Approved
0.597 Remote Similarity NPD7641 Discontinued
0.5966 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5952 Remote Similarity NPD1407 Approved
0.5899 Remote Similarity NPD8273 Phase 1
0.5859 Remote Similarity NPD6640 Phase 3
0.5797 Remote Similarity NPD7623 Phase 3
0.5797 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5745 Remote Similarity NPD7747 Phase 1
0.5745 Remote Similarity NPD8074 Phase 3
0.5745 Remote Similarity NPD7746 Phase 1
0.5725 Remote Similarity NPD8513 Phase 3
0.5725 Remote Similarity NPD7503 Approved
0.5725 Remote Similarity NPD8517 Approved
0.5725 Remote Similarity NPD8515 Approved
0.5725 Remote Similarity NPD8516 Approved
0.5725 Remote Similarity NPD8444 Approved
0.5702 Remote Similarity NPD6698 Approved
0.5702 Remote Similarity NPD46 Approved
0.5685 Remote Similarity NPD8415 Approved
0.5662 Remote Similarity NPD7500 Approved
0.5649 Remote Similarity NPD7274 Clinical (unspecified phase)
0.5615 Remote Similarity NPD4211 Phase 1
0.5612 Remote Similarity NPD7739 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