Structure

Physi-Chem Properties

Molecular Weight:  551.19
Volume:  496.803
LogP:  -0.59
LogD:  -0.382
LogS:  -1.445
# Rotatable Bonds:  8
TPSA:  220.56
# H-Bond Aceptor:  16
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.19
Synthetic Accessibility Score:  5.606
Fsp3:  0.609
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.249
MDCK Permeability:  4.712880763690919e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.981
Human Intestinal Absorption (HIA):  0.973
20% Bioavailability (F20%):  0.31
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.361
Plasma Protein Binding (PPB):  22.582408905029297%
Volume Distribution (VD):  0.947
Pgp-substrate:  72.07189178466797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.015
CYP1A2-substrate:  0.585
CYP2C19-inhibitor:  0.054
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.013
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.054
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.165

ADMET: Excretion

Clearance (CL):  4.203
Half-life (T1/2):  0.897

ADMET: Toxicity

hERG Blockers:  0.048
Human Hepatotoxicity (H-HT):  0.959
Drug-inuced Liver Injury (DILI):  0.992
AMES Toxicity:  0.17
Rat Oral Acute Toxicity:  0.307
Maximum Recommended Daily Dose:  0.036
Skin Sensitization:  0.283
Carcinogencity:  0.033
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.773

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

  Natural Product: NPC157821

Natural Product ID:  NPC157821
Common Name*:   LOWKANMKNQBRPJ-MRAUHCMASA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  LOWKANMKNQBRPJ-MRAUHCMASA-N
Standard InCHI:  InChI=1S/C23H29N5O11/c1-4-9(6-29)21(31)38-17-13(30)15(22(32)35-3)37-11-5-10-14(39-23(11,17)33)16(34-2)20(36-10)28-8-27-12-18(24)25-7-26-19(12)28/h4,7-8,10-11,13-17,20,29-30,33H,5-6H2,1-3H3,(H2,24,25,26)/b9-4+/t10-,11-,13-,14+,15+,16-,17+,20-,23-/m1/s1
SMILES:  CO[C@@H]1[C@H]2O[C@]3(O)[C@@H](C[C@H]2O[C@H]1n1cnc2c1ncnc2N)O[C@@H]([C@H]([C@@H]3OC(=O)/C(=C/C)/CO)O)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3109448
PubChem CID:   6441694
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:0002203] Glycosylamines

*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
NPO32887 Streptomyces sp. L-9-10 Species Streptomycetaceae Bacteria organic extract n.a. n.a. PMID[24533857]
NPO40215 Streptomyces sp. CB01388 Strain Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[29469575]

☑ 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
NPT71 Cell Line HEK293 Homo sapiens IC50 = 2700.0 nM PMID[543795]
NPT180 Cell Line HCT-8 Homo sapiens EC50 > 25000.0 nM PMID[543796]
NPT2615 Cell Line HEK-293T Homo sapiens CC50 > 40000.0 nM PMID[543796]
NPT65 Cell Line HepG2 Homo sapiens CC50 > 40000.0 nM PMID[543796]
NPT2 Others Unspecified IC50 = 1800.0 nM PMID[543795]
NPT2 Others Unspecified Inhibition = 45.8 % PMID[543795]
NPT2 Others Unspecified Inhibition = 80.9 % PMID[543795]
NPT1022 Organism Cryptosporidium parvum Cryptosporidium parvum EC50 = 16000.0 nM PMID[543796]
NPT1022 Organism Cryptosporidium parvum Cryptosporidium parvum EC50 = 21000.0 nM PMID[543796]

☑ 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 NPC157821 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
0.9944 High Similarity NPC5802
0.9889 High Similarity NPC276373
0.9222 High Similarity NPC282458
0.9222 High Similarity NPC78941
0.9056 High Similarity NPC24589
0.766 Intermediate Similarity NPC290959
0.7459 Intermediate Similarity NPC239737
0.7253 Intermediate Similarity NPC309832
0.7253 Intermediate Similarity NPC219313
0.7214 Intermediate Similarity NPC313514
0.7198 Intermediate Similarity NPC189068
0.7143 Intermediate Similarity NPC21448
0.7143 Intermediate Similarity NPC107374
0.7143 Intermediate Similarity NPC156461
0.7135 Intermediate Similarity NPC150853
0.7111 Intermediate Similarity NPC317821
0.7104 Intermediate Similarity NPC164665
0.7098 Intermediate Similarity NPC325906
0.7065 Intermediate Similarity NPC269827
0.7056 Intermediate Similarity NPC313897
0.7047 Intermediate Similarity NPC324484
0.7033 Intermediate Similarity NPC229974
0.7021 Intermediate Similarity NPC212551
0.7021 Intermediate Similarity NPC302778
0.6995 Remote Similarity NPC323091
0.6984 Remote Similarity NPC174802
0.6947 Remote Similarity NPC224076
0.6931 Remote Similarity NPC130586
0.6931 Remote Similarity NPC164952
0.6923 Remote Similarity NPC161659
0.6923 Remote Similarity NPC209525
0.6915 Remote Similarity NPC85689
0.6915 Remote Similarity NPC211025
0.6915 Remote Similarity NPC185991
0.6911 Remote Similarity NPC226245
0.6878 Remote Similarity NPC472816
0.6878 Remote Similarity NPC321814
0.6868 Remote Similarity NPC129756
0.6848 Remote Similarity NPC314152
0.6825 Remote Similarity NPC161224
0.6823 Remote Similarity NPC316618
0.6809 Remote Similarity NPC136349
0.6789 Remote Similarity NPC207633
0.6755 Remote Similarity NPC121222
0.6736 Remote Similarity NPC54320
0.6736 Remote Similarity NPC313754
0.6736 Remote Similarity NPC311197
0.6716 Remote Similarity NPC326529
0.6702 Remote Similarity NPC328479
0.6701 Remote Similarity NPC195140
0.6684 Remote Similarity NPC52238
0.6683 Remote Similarity NPC324198
0.6683 Remote Similarity NPC319100
0.6683 Remote Similarity NPC189261
0.663 Remote Similarity NPC33996
0.66 Remote Similarity NPC326082
0.6583 Remote Similarity NPC261595
0.6564 Remote Similarity NPC93365
0.655 Remote Similarity NPC324033
0.655 Remote Similarity NPC321458
0.6481 Remote Similarity NPC21461
0.6432 Remote Similarity NPC320818
0.641 Remote Similarity NPC160666
0.6359 Remote Similarity NPC321052
0.6332 Remote Similarity NPC250178
0.6303 Remote Similarity NPC265111
0.6268 Remote Similarity NPC473585
0.6263 Remote Similarity NPC472833
0.625 Remote Similarity NPC18308
0.625 Remote Similarity NPC472832
0.624 Remote Similarity NPC150447
0.617 Remote Similarity NPC61198
0.6131 Remote Similarity NPC472834
0.6117 Remote Similarity NPC262926
0.6105 Remote Similarity NPC30326
0.6096 Remote Similarity NPC57279
0.6091 Remote Similarity NPC326694
0.6087 Remote Similarity NPC222174
0.6082 Remote Similarity NPC89147
0.6082 Remote Similarity NPC274384
0.6076 Remote Similarity NPC107160
0.6058 Remote Similarity NPC158055
0.6051 Remote Similarity NPC232408
0.6051 Remote Similarity NPC64705
0.6048 Remote Similarity NPC164845
0.6045 Remote Similarity NPC233431
0.6045 Remote Similarity NPC300139
0.6031 Remote Similarity NPC211820
0.6031 Remote Similarity NPC251233
0.6019 Remote Similarity NPC133782
0.6019 Remote Similarity NPC144474
0.6019 Remote Similarity NPC527
0.6 Remote Similarity NPC317746
0.6 Remote Similarity NPC177169
0.599 Remote Similarity NPC168702
0.599 Remote Similarity NPC125659
0.5979 Remote Similarity NPC319221
0.5951 Remote Similarity NPC14590
0.5949 Remote Similarity NPC318590
0.5944 Remote Similarity NPC324815
0.5942 Remote Similarity NPC33382
0.5929 Remote Similarity NPC103388
0.5928 Remote Similarity NPC186619
0.5926 Remote Similarity NPC324009
0.5897 Remote Similarity NPC74306
0.5897 Remote Similarity NPC315642
0.5853 Remote Similarity NPC101676
0.5825 Remote Similarity NPC321393
0.5817 Remote Similarity NPC315126
0.5817 Remote Similarity NPC314774
0.5737 Remote Similarity NPC246193
0.5702 Remote Similarity NPC54537
0.5663 Remote Similarity NPC296437
0.5657 Remote Similarity NPC476528
0.5657 Remote Similarity NPC476433
0.5635 Remote Similarity NPC470266
0.5628 Remote Similarity NPC476520
0.5628 Remote Similarity NPC476013
0.5628 Remote Similarity NPC476522
0.5628 Remote Similarity NPC474986
0.5622 Remote Similarity NPC476408
0.5615 Remote Similarity NPC476832
0.5615 Remote Similarity NPC472436
0.56 Remote Similarity NPC476521

  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 NPC157821 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
0.7692 Intermediate Similarity NPD5682 Phase 3
0.7692 Intermediate Similarity NPD5683 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD5684 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD3083 Approved
0.7297 Intermediate Similarity NPD3107 Discontinued
0.7273 Intermediate Similarity NPD2646 Discontinued
0.7214 Intermediate Similarity NPD7138 Phase 2
0.7143 Intermediate Similarity NPD250 Approved
0.7143 Intermediate Similarity NPD249 Approved
0.7098 Intermediate Similarity NPD1776 Approved
0.7098 Intermediate Similarity NPD1777 Approved
0.7085 Intermediate Similarity NPD4716 Approved
0.7065 Intermediate Similarity NPD195 Approved
0.7065 Intermediate Similarity NPD186 Discovery
0.7056 Intermediate Similarity NPD5666 Phase 2
0.705 Intermediate Similarity NPD4744 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD1369 Phase 2
0.701 Intermediate Similarity NPD7988 Suspended
0.7 Intermediate Similarity NPD2624 Phase 2
0.6984 Remote Similarity NPD339 Approved
0.6974 Remote Similarity NPD2647 Phase 3
0.6947 Remote Similarity NPD169 Phase 2
0.6931 Remote Similarity NPD338 Approved
0.6931 Remote Similarity NPD1750 Clinical (unspecified phase)
0.6915 Remote Similarity NPD283 Approved
0.6891 Remote Similarity NPD516 Clinical (unspecified phase)
0.6848 Remote Similarity NPD185 Approved
0.6842 Remote Similarity NPD242 Approved
0.6829 Remote Similarity NPD6417 Clinical (unspecified phase)
0.6823 Remote Similarity NPD1732 Phase 3
0.6809 Remote Similarity NPD548 Clinical (unspecified phase)
0.6774 Remote Similarity NPD166 Approved
0.6748 Remote Similarity NPD6023 Discontinued
0.6739 Remote Similarity NPD193 Suspended
0.6736 Remote Similarity NPD218 Approved
0.6736 Remote Similarity NPD216 Approved
0.6736 Remote Similarity NPD217 Approved
0.6736 Remote Similarity NPD219 Phase 3
0.6736 Remote Similarity NPD220 Clinical (unspecified phase)
0.6732 Remote Similarity NPD1692 Approved
0.6709 Remote Similarity NPD8291 Clinical (unspecified phase)
0.6709 Remote Similarity NPD8375 Approved
0.6684 Remote Similarity NPD3708 Phase 2
0.6683 Remote Similarity NPD4171 Clinical (unspecified phase)
0.6653 Remote Similarity NPD8371 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5080 Phase 2
0.6596 Remote Similarity NPD7158 Phase 1
0.6583 Remote Similarity NPD247 Clinical (unspecified phase)
0.658 Remote Similarity NPD213 Clinical (unspecified phase)
0.658 Remote Similarity NPD214 Approved
0.6564 Remote Similarity NPD546 Clinical (unspecified phase)
0.6562 Remote Similarity NPD5079 Phase 2
0.656 Remote Similarity NPD2965 Clinical (unspecified phase)
0.6493 Remote Similarity NPD4054 Clinical (unspecified phase)
0.6488 Remote Similarity NPD1412 Clinical (unspecified phase)
0.6455 Remote Similarity NPD2877 Clinical (unspecified phase)
0.6455 Remote Similarity NPD2876 Phase 3
0.6429 Remote Similarity NPD2903 Clinical (unspecified phase)
0.6429 Remote Similarity NPD2902 Phase 2
0.6396 Remote Similarity NPD2824 Phase 2
0.6392 Remote Similarity NPD7842 Phase 2
0.638 Remote Similarity NPD7323 Phase 2
0.6368 Remote Similarity NPD4240 Approved
0.6345 Remote Similarity NPD8409 Suspended
0.6339 Remote Similarity NPD248 Discontinued
0.6296 Remote Similarity NPD3695 Approved
0.6296 Remote Similarity NPD3696 Approved
0.6296 Remote Similarity NPD549 Approved
0.6291 Remote Similarity NPD2632 Approved
0.6291 Remote Similarity NPD2630 Approved
0.6291 Remote Similarity NPD2631 Clinical (unspecified phase)
0.6256 Remote Similarity NPD5665 Clinical (unspecified phase)
0.625 Remote Similarity NPD171 Discontinued
0.625 Remote Similarity NPD9632 Phase 3
0.617 Remote Similarity NPD252 Clinical (unspecified phase)
0.6094 Remote Similarity NPD1430 Approved
0.6094 Remote Similarity NPD1431 Approved
0.6058 Remote Similarity NPD6840 Approved
0.6054 Remote Similarity NPD870 Clinical (unspecified phase)
0.604 Remote Similarity NPD4074 Clinical (unspecified phase)
0.6032 Remote Similarity NPD8373 Clinical (unspecified phase)
0.603 Remote Similarity NPD536 Clinical (unspecified phase)
0.6022 Remote Similarity NPD9633 Phase 3
0.5991 Remote Similarity NPD1046 Clinical (unspecified phase)
0.5991 Remote Similarity NPD2152 Clinical (unspecified phase)
0.598 Remote Similarity NPD3086 Phase 3
0.596 Remote Similarity NPD7850 Discontinued
0.596 Remote Similarity NPD7851 Phase 1
0.5957 Remote Similarity NPD6763 Discontinued
0.5947 Remote Similarity NPD194 Clinical (unspecified phase)
0.5944 Remote Similarity NPD8250 Phase 2
0.5939 Remote Similarity NPD7531 Clinical (unspecified phase)
0.5938 Remote Similarity NPD1808 Phase 1
0.593 Remote Similarity NPD3085 Phase 1
0.5915 Remote Similarity NPD4555 Clinical (unspecified phase)
0.5913 Remote Similarity NPD4495 Phase 1
0.5911 Remote Similarity NPD4458 Phase 2
0.5911 Remote Similarity NPD4459 Clinical (unspecified phase)
0.5897 Remote Similarity NPD582 Approved
0.5885 Remote Similarity NPD5486 Discontinued
0.5871 Remote Similarity NPD9605 Phase 3
0.586 Remote Similarity NPD9408 Phase 3
0.5857 Remote Similarity NPD4896 Clinical (unspecified phase)
0.5833 Remote Similarity NPD1121 Approved
0.5833 Remote Similarity NPD1120 Approved
0.5826 Remote Similarity NPD1063 Phase 2
0.5808 Remote Similarity NPD1730 Discontinued
0.5808 Remote Similarity NPD5458 Discontinued
0.5798 Remote Similarity NPD6381 Phase 2
0.5792 Remote Similarity NPD231 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4715 Clinical (unspecified phase)
0.5789 Remote Similarity NPD34 Approved
0.5789 Remote Similarity NPD4713 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4714 Approved
0.5785 Remote Similarity NPD1571 Phase 2
0.5776 Remote Similarity NPD5072 Discontinued
0.5774 Remote Similarity NPD6036 Suspended
0.5771 Remote Similarity NPD8421 Discontinued
0.5737 Remote Similarity NPD7197 Approved
0.5732 Remote Similarity NPD7502 Clinical (unspecified phase)
0.5731 Remote Similarity NPD6351 Discovery
0.5721 Remote Similarity NPD2593 Clinical (unspecified phase)
0.5714 Remote Similarity NPD2453 Phase 2
0.5714 Remote Similarity NPD2451 Phase 2
0.5714 Remote Similarity NPD2450 Phase 2
0.5714 Remote Similarity NPD1572 Phase 2
0.5714 Remote Similarity NPD7486 Phase 1
0.5714 Remote Similarity NPD2452 Phase 2
0.5703 Remote Similarity NPD8370 Discontinued
0.5702 Remote Similarity NPD5887 Clinical (unspecified phase)
0.5696 Remote Similarity NPD8271 Discontinued
0.5668 Remote Similarity NPD8329 Phase 3
0.5665 Remote Similarity NPD353 Discontinued
0.5663 Remote Similarity NPD4938 Phase 2
0.565 Remote Similarity NPD8119 Discontinued
0.563 Remote Similarity NPD8325 Phase 3
0.563 Remote Similarity NPD8326 Phase 3
0.563 Remote Similarity NPD8327 Clinical (unspecified phase)
0.5628 Remote Similarity NPD7103 Approved
0.5625 Remote Similarity NPD4950 Approved
0.5625 Remote Similarity NPD5321 Phase 3
0.5625 Remote Similarity NPD5827 Discontinued
0.5613 Remote Similarity NPD7198 Clinical (unspecified phase)
0.5606 Remote Similarity NPD2253 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