Structure

Physi-Chem Properties

Molecular Weight:  453.29
Volume:  506.717
LogP:  1.588
LogD:  2.312
LogS:  -3.98
# Rotatable Bonds:  4
TPSA:  89.79
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.476
Synthetic Accessibility Score:  5.262
Fsp3:  0.393
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.951
MDCK Permeability:  3.742867920664139e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.857
20% Bioavailability (F20%):  0.971
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.042
Plasma Protein Binding (PPB):  92.160888671875%
Volume Distribution (VD):  0.532
Pgp-substrate:  5.348637104034424%

ADMET: Metabolism

CYP1A2-inhibitor:  0.526
CYP1A2-substrate:  0.076
CYP2C19-inhibitor:  0.322
CYP2C19-substrate:  0.231
CYP2C9-inhibitor:  0.338
CYP2C9-substrate:  0.999
CYP2D6-inhibitor:  0.889
CYP2D6-substrate:  0.942
CYP3A4-inhibitor:  0.731
CYP3A4-substrate:  0.038

ADMET: Excretion

Clearance (CL):  0.861
Half-life (T1/2):  0.351

ADMET: Toxicity

hERG Blockers:  0.278
Human Hepatotoxicity (H-HT):  0.819
Drug-inuced Liver Injury (DILI):  0.064
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.026
Maximum Recommended Daily Dose:  0.97
Skin Sensitization:  0.868
Carcinogencity:  0.309
Eye Corrosion:  0.003
Eye Irritation:  0.018
Respiratory Toxicity:  0.879

Download Data

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

  Natural Product: NPC314678

Natural Product ID:  NPC314678
Common Name*:   Aureoverticillactam
IUPAC Name:   (3E,5E,7E,13Z,15E,17E,19E)-22-[(E)-hex-2-enyl]-9,10,12-trihydroxy-17-methyl-1-azacyclodocosa-3,5,7,13,15,17,19-heptaen-2-one
Synonyms:   Aureoverticillactam
Standard InCHIKey:  VMKRIAILWBEBLR-TWCCLTHVSA-N
Standard InCHI:  InChI=1S/C28H39NO4/c1-3-4-5-8-17-24-18-13-11-15-23(2)16-12-14-19-25(30)22-27(32)26(31)20-9-6-7-10-21-28(33)29-24/h5-16,19-21,24-27,30-32H,3-4,17-18,22H2,1-2H3,(H,29,33)/b7-6+,8-5+,13-11+,16-12+,19-14-,20-9+,21-10+,23-15+
SMILES:  CCC/C=C/CC1C/C=C/C=C(C)/C=C/C=CC(CC(C(/C=C/C=C/C=C/C(=N1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL458037
PubChem CID:   9868536
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000064] Macrolactams

*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
NPO16612 Streptomyces aureoverticillatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15332863]
NPO16612 Streptomyces aureoverticillatus Species Streptomycetaceae Bacteria 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
NPT139 Cell Line HT-29 Homo sapiens EC50 = 3600.0 nM PMID[505619]
NPT169 Cell Line B16-F10 Mus musculus EC50 = 2200.0 nM PMID[505619]
NPT15 Cell Line Jurkat Homo sapiens EC50 = 2300.0 nM PMID[505619]

☑ 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 NPC314678 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
0.9104 High Similarity NPC315141
0.9104 High Similarity NPC129995
0.8406 Intermediate Similarity NPC477525
0.8261 Intermediate Similarity NPC253468
0.8261 Intermediate Similarity NPC235311
0.8116 Intermediate Similarity NPC471023
0.8 Intermediate Similarity NPC288086
0.7703 Intermediate Similarity NPC291196
0.7703 Intermediate Similarity NPC103712
0.7561 Intermediate Similarity NPC228638
0.7467 Intermediate Similarity NPC471022
0.7465 Intermediate Similarity NPC29468
0.7436 Intermediate Similarity NPC217095
0.7436 Intermediate Similarity NPC264417
0.7333 Intermediate Similarity NPC45313
0.7326 Intermediate Similarity NPC316186
0.7324 Intermediate Similarity NPC130807
0.7183 Intermediate Similarity NPC312826
0.7143 Intermediate Similarity NPC183449
0.7143 Intermediate Similarity NPC197294
0.7143 Intermediate Similarity NPC8098
0.7111 Intermediate Similarity NPC262312
0.7111 Intermediate Similarity NPC35269
0.7111 Intermediate Similarity NPC23454
0.7111 Intermediate Similarity NPC70323
0.7101 Intermediate Similarity NPC242930
0.7101 Intermediate Similarity NPC297020
0.7059 Intermediate Similarity NPC303672
0.7059 Intermediate Similarity NPC477199
0.7 Intermediate Similarity NPC24216
0.7 Intermediate Similarity NPC306420
0.7 Intermediate Similarity NPC261158
0.7 Intermediate Similarity NPC104138
0.6957 Remote Similarity NPC132669
0.6957 Remote Similarity NPC269800
0.6957 Remote Similarity NPC44193
0.6957 Remote Similarity NPC246519
0.6957 Remote Similarity NPC184014
0.6957 Remote Similarity NPC14234
0.6944 Remote Similarity NPC150505
0.6944 Remote Similarity NPC74617
0.6923 Remote Similarity NPC192066
0.6923 Remote Similarity NPC158445
0.6923 Remote Similarity NPC256570
0.6923 Remote Similarity NPC17290
0.6923 Remote Similarity NPC157353
0.6923 Remote Similarity NPC156782
0.6923 Remote Similarity NPC282088
0.6923 Remote Similarity NPC3568
0.6923 Remote Similarity NPC54961
0.6912 Remote Similarity NPC195986
0.6905 Remote Similarity NPC82799
0.6892 Remote Similarity NPC55068
0.6889 Remote Similarity NPC182632
0.6889 Remote Similarity NPC282705
0.6857 Remote Similarity NPC273023
0.6857 Remote Similarity NPC471992
0.6849 Remote Similarity NPC6795
0.6848 Remote Similarity NPC50902
0.6848 Remote Similarity NPC233273
0.6848 Remote Similarity NPC205546
0.6806 Remote Similarity NPC321030
0.6778 Remote Similarity NPC139782
0.6778 Remote Similarity NPC74672
0.6778 Remote Similarity NPC242503
0.6778 Remote Similarity NPC43074
0.6778 Remote Similarity NPC209047
0.6774 Remote Similarity NPC175614
0.6765 Remote Similarity NPC54542
0.6765 Remote Similarity NPC304223
0.6765 Remote Similarity NPC267340
0.6765 Remote Similarity NPC243539
0.6765 Remote Similarity NPC145032
0.6712 Remote Similarity NPC325550
0.6712 Remote Similarity NPC329003
0.6712 Remote Similarity NPC326524
0.6703 Remote Similarity NPC473604
0.6703 Remote Similarity NPC186840
0.6703 Remote Similarity NPC473581
0.6703 Remote Similarity NPC309898
0.6703 Remote Similarity NPC475125
0.6703 Remote Similarity NPC15851
0.6703 Remote Similarity NPC111567
0.6703 Remote Similarity NPC263545
0.6703 Remote Similarity NPC473950
0.6667 Remote Similarity NPC189764
0.662 Remote Similarity NPC471991
0.6618 Remote Similarity NPC267692
0.6618 Remote Similarity NPC307435
0.6585 Remote Similarity NPC62293
0.6585 Remote Similarity NPC51055
0.6585 Remote Similarity NPC140327
0.6585 Remote Similarity NPC212008
0.6585 Remote Similarity NPC476924
0.6582 Remote Similarity NPC280065
0.6582 Remote Similarity NPC45060
0.6571 Remote Similarity NPC474496
0.6571 Remote Similarity NPC119655
0.6569 Remote Similarity NPC29501
0.6548 Remote Similarity NPC474833
0.6531 Remote Similarity NPC55336
0.6522 Remote Similarity NPC473672
0.6522 Remote Similarity NPC474495
0.6522 Remote Similarity NPC200772
0.65 Remote Similarity NPC324638
0.6489 Remote Similarity NPC469739
0.6486 Remote Similarity NPC322186
0.6479 Remote Similarity NPC167759
0.6479 Remote Similarity NPC163912
0.6479 Remote Similarity NPC56028
0.6479 Remote Similarity NPC305288
0.6463 Remote Similarity NPC315843
0.6456 Remote Similarity NPC249713
0.6447 Remote Similarity NPC477106
0.6437 Remote Similarity NPC474312
0.641 Remote Similarity NPC187315
0.64 Remote Similarity NPC258788
0.64 Remote Similarity NPC201128
0.6395 Remote Similarity NPC207657
0.6389 Remote Similarity NPC329686
0.6351 Remote Similarity NPC226848
0.6337 Remote Similarity NPC315426
0.6316 Remote Similarity NPC273614
0.6304 Remote Similarity NPC39290
0.6304 Remote Similarity NPC159369
0.6301 Remote Similarity NPC477049
0.63 Remote Similarity NPC74035
0.6286 Remote Similarity NPC71053
0.6286 Remote Similarity NPC59408
0.6269 Remote Similarity NPC160628
0.6269 Remote Similarity NPC140501
0.6265 Remote Similarity NPC474545
0.6265 Remote Similarity NPC24590
0.6265 Remote Similarity NPC107654
0.625 Remote Similarity NPC123669
0.625 Remote Similarity NPC13011
0.625 Remote Similarity NPC110732
0.625 Remote Similarity NPC124382
0.6237 Remote Similarity NPC477866
0.6237 Remote Similarity NPC477865
0.6234 Remote Similarity NPC77891
0.622 Remote Similarity NPC316185
0.6216 Remote Similarity NPC52012
0.6216 Remote Similarity NPC245650
0.6203 Remote Similarity NPC113224
0.6203 Remote Similarity NPC146811
0.6197 Remote Similarity NPC35756
0.6196 Remote Similarity NPC34754
0.617 Remote Similarity NPC61894
0.617 Remote Similarity NPC475603
0.6164 Remote Similarity NPC281590
0.6164 Remote Similarity NPC227135
0.6154 Remote Similarity NPC475221
0.6143 Remote Similarity NPC328784
0.6143 Remote Similarity NPC474460
0.6143 Remote Similarity NPC291437
0.6133 Remote Similarity NPC181872
0.6133 Remote Similarity NPC325734
0.6125 Remote Similarity NPC73603
0.6119 Remote Similarity NPC138935
0.6111 Remote Similarity NPC161670
0.6111 Remote Similarity NPC475975
0.6104 Remote Similarity NPC324077
0.6104 Remote Similarity NPC47333
0.6098 Remote Similarity NPC473361
0.6098 Remote Similarity NPC329904
0.6098 Remote Similarity NPC474674
0.6092 Remote Similarity NPC314762
0.6092 Remote Similarity NPC314854
0.6092 Remote Similarity NPC313911
0.6082 Remote Similarity NPC475503
0.6076 Remote Similarity NPC308844
0.6067 Remote Similarity NPC477385
0.6067 Remote Similarity NPC477390
0.6058 Remote Similarity NPC298484
0.6056 Remote Similarity NPC93639
0.6053 Remote Similarity NPC122239
0.6053 Remote Similarity NPC475931
0.6053 Remote Similarity NPC318306
0.6053 Remote Similarity NPC322002
0.6053 Remote Similarity NPC329249
0.6049 Remote Similarity NPC63873
0.6049 Remote Similarity NPC23721
0.6023 Remote Similarity NPC311369
0.6 Remote Similarity NPC319473
0.6 Remote Similarity NPC313234
0.6 Remote Similarity NPC251122
0.6 Remote Similarity NPC323436
0.6 Remote Similarity NPC3094
0.5977 Remote Similarity NPC475980
0.5976 Remote Similarity NPC329989
0.5976 Remote Similarity NPC127145
0.5976 Remote Similarity NPC474675
0.5976 Remote Similarity NPC137620
0.5976 Remote Similarity NPC475930
0.5976 Remote Similarity NPC239373
0.5974 Remote Similarity NPC327112
0.5974 Remote Similarity NPC309877
0.597 Remote Similarity NPC116934
0.5955 Remote Similarity NPC226982

  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 NPC314678 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
0.6892 Remote Similarity NPD3210 Clinical (unspecified phase)
0.6778 Remote Similarity NPD8522 Clinical (unspecified phase)
0.65 Remote Similarity NPD3212 Clinical (unspecified phase)
0.6269 Remote Similarity NPD4265 Approved
0.61 Remote Similarity NPD244 Clinical (unspecified phase)
0.6078 Remote Similarity NPD6640 Phase 3
0.6 Remote Similarity NPD6421 Discontinued
0.5974 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5962 Remote Similarity NPD6406 Approved
0.5926 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5921 Remote Similarity NPD585 Clinical (unspecified phase)
0.5895 Remote Similarity NPD6095 Approved
0.5895 Remote Similarity NPD6094 Approved
0.5818 Remote Similarity NPD7505 Discontinued
0.5794 Remote Similarity NPD7601 Clinical (unspecified phase)
0.5765 Remote Similarity NPD4732 Discontinued
0.5758 Remote Similarity NPD4228 Discovery
0.575 Remote Similarity NPD277 Approved
0.5652 Remote Similarity NPD205 Approved
0.5648 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5632 Remote Similarity NPD8264 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