Structure

Physi-Chem Properties

Molecular Weight:  304.2
Volume:  341.812
LogP:  4.863
LogD:  5.017
LogS:  -5.222
# Rotatable Bonds:  7
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.732
Synthetic Accessibility Score:  3.739
Fsp3:  0.526
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.732
MDCK Permeability:  2.1844667571713217e-05
Pgp-inhibitor:  0.029
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.309

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.126
Plasma Protein Binding (PPB):  100.09224700927734%
Volume Distribution (VD):  2.31
Pgp-substrate:  2.1616811752319336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.731
CYP1A2-substrate:  0.915
CYP2C19-inhibitor:  0.822
CYP2C19-substrate:  0.851
CYP2C9-inhibitor:  0.873
CYP2C9-substrate:  0.978
CYP2D6-inhibitor:  0.167
CYP2D6-substrate:  0.877
CYP3A4-inhibitor:  0.697
CYP3A4-substrate:  0.27

ADMET: Excretion

Clearance (CL):  2.3
Half-life (T1/2):  0.397

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.975
Drug-inuced Liver Injury (DILI):  0.834
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.146
Maximum Recommended Daily Dose:  0.651
Skin Sensitization:  0.555
Carcinogencity:  0.248
Eye Corrosion:  0.004
Eye Irritation:  0.027
Respiratory Toxicity:  0.342

Download Data

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

  Natural Product: NPC471566

Natural Product ID:  NPC471566
Common Name*:   Iromycin Ao
IUPAC Name:   6-[(2E,5E)-3,7-dimethylocta-2,5-dienyl]-4-hydroxy-3-methyl-5-propylpyran-2-one
Synonyms:   iromycin AO
Standard InCHIKey:  RSPHANBIMXMURX-DTCTWCMCSA-N
Standard InCHI:  InChI=1S/C19H28O3/c1-6-8-16-17(22-19(21)15(5)18(16)20)12-11-14(4)10-7-9-13(2)3/h7,9,11,13,20H,6,8,10,12H2,1-5H3/b9-7+,14-11+
SMILES:  CCCC1=C(OC(=O)C(=C1O)C)CC=C(C)CC=CC(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL258095
PubChem CID:   54732496
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000086] Pyrans
        • [CHEMONTID:0000481] Pyranones 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
NPO33217 streptomyces sp. dra 17 Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18054490]

☑ 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
NPT5098 Protein Complex Mitochondrial complex I; NADH oxidoreductase Bos taurus IC50 > 26600.0 nM PMID[560061]

☑ 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 NPC471566 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
0.9672 High Similarity NPC471565
0.9355 High Similarity NPC471556
0.8657 High Similarity NPC59558
0.8615 High Similarity NPC315115
0.8358 Intermediate Similarity NPC313444
0.8333 Intermediate Similarity NPC218486
0.8254 Intermediate Similarity NPC133600
0.8209 Intermediate Similarity NPC132286
0.8116 Intermediate Similarity NPC315597
0.8116 Intermediate Similarity NPC316029
0.8088 Intermediate Similarity NPC238223
0.7903 Intermediate Similarity NPC173157
0.7879 Intermediate Similarity NPC2328
0.7857 Intermediate Similarity NPC315285
0.7826 Intermediate Similarity NPC79220
0.7812 Intermediate Similarity NPC189700
0.7778 Intermediate Similarity NPC86948
0.7778 Intermediate Similarity NPC221763
0.7746 Intermediate Similarity NPC316185
0.7714 Intermediate Similarity NPC151481
0.7714 Intermediate Similarity NPC473277
0.7705 Intermediate Similarity NPC191643
0.7703 Intermediate Similarity NPC315394
0.7647 Intermediate Similarity NPC220766
0.7639 Intermediate Similarity NPC316851
0.7612 Intermediate Similarity NPC473737
0.7576 Intermediate Similarity NPC130953
0.7571 Intermediate Similarity NPC474823
0.7538 Intermediate Similarity NPC254095
0.7536 Intermediate Similarity NPC146811
0.7536 Intermediate Similarity NPC470033
0.7536 Intermediate Similarity NPC191233
0.7536 Intermediate Similarity NPC37382
0.7534 Intermediate Similarity NPC470686
0.7534 Intermediate Similarity NPC315843
0.75 Intermediate Similarity NPC234084
0.75 Intermediate Similarity NPC475618
0.75 Intermediate Similarity NPC126184
0.75 Intermediate Similarity NPC150717
0.75 Intermediate Similarity NPC51846
0.7467 Intermediate Similarity NPC316324
0.7465 Intermediate Similarity NPC475004
0.7463 Intermediate Similarity NPC15193
0.7432 Intermediate Similarity NPC315552
0.7432 Intermediate Similarity NPC478193
0.7432 Intermediate Similarity NPC478192
0.7432 Intermediate Similarity NPC478195
0.7432 Intermediate Similarity NPC478196
0.7432 Intermediate Similarity NPC478194
0.7432 Intermediate Similarity NPC478191
0.7391 Intermediate Similarity NPC96414
0.7391 Intermediate Similarity NPC182794
0.7391 Intermediate Similarity NPC273600
0.7391 Intermediate Similarity NPC282760
0.7391 Intermediate Similarity NPC7940
0.7385 Intermediate Similarity NPC249850
0.7385 Intermediate Similarity NPC135863
0.7385 Intermediate Similarity NPC293437
0.7353 Intermediate Similarity NPC68110
0.7344 Intermediate Similarity NPC478117
0.7333 Intermediate Similarity NPC128520
0.7324 Intermediate Similarity NPC477117
0.7324 Intermediate Similarity NPC287705
0.7313 Intermediate Similarity NPC429928
0.7313 Intermediate Similarity NPC98519
0.7313 Intermediate Similarity NPC309408
0.7297 Intermediate Similarity NPC107654
0.7286 Intermediate Similarity NPC201356
0.7273 Intermediate Similarity NPC474084
0.7273 Intermediate Similarity NPC223679
0.726 Intermediate Similarity NPC293114
0.726 Intermediate Similarity NPC178575
0.7258 Intermediate Similarity NPC43053
0.7222 Intermediate Similarity NPC470693
0.7206 Intermediate Similarity NPC26810
0.7188 Intermediate Similarity NPC478120
0.7188 Intermediate Similarity NPC474127
0.7164 Intermediate Similarity NPC82465
0.7162 Intermediate Similarity NPC284006
0.7143 Intermediate Similarity NPC315765
0.7125 Intermediate Similarity NPC475083
0.7125 Intermediate Similarity NPC16488
0.7123 Intermediate Similarity NPC473361
0.7123 Intermediate Similarity NPC476037
0.7123 Intermediate Similarity NPC329904
0.7123 Intermediate Similarity NPC202011
0.7121 Intermediate Similarity NPC129150
0.7121 Intermediate Similarity NPC294938
0.7105 Intermediate Similarity NPC470705
0.7101 Intermediate Similarity NPC179087
0.7101 Intermediate Similarity NPC210303
0.7101 Intermediate Similarity NPC475073
0.7101 Intermediate Similarity NPC44343
0.7097 Intermediate Similarity NPC221467
0.7077 Intermediate Similarity NPC25038
0.7073 Intermediate Similarity NPC315395
0.7073 Intermediate Similarity NPC316426
0.7059 Intermediate Similarity NPC79756
0.7059 Intermediate Similarity NPC26223
0.7042 Intermediate Similarity NPC475675
0.7042 Intermediate Similarity NPC475555
0.7015 Intermediate Similarity NPC21946
0.7013 Intermediate Similarity NPC473825
0.7 Intermediate Similarity NPC477456
0.7 Intermediate Similarity NPC477457
0.6986 Remote Similarity NPC232812
0.6984 Remote Similarity NPC148056
0.6977 Remote Similarity NPC282644
0.6977 Remote Similarity NPC29798
0.6974 Remote Similarity NPC260396
0.697 Remote Similarity NPC472808
0.697 Remote Similarity NPC324224
0.6957 Remote Similarity NPC151648
0.6957 Remote Similarity NPC55376
0.6951 Remote Similarity NPC471223
0.6951 Remote Similarity NPC67081
0.6944 Remote Similarity NPC21998
0.6944 Remote Similarity NPC122627
0.6933 Remote Similarity NPC12815
0.6933 Remote Similarity NPC329890
0.6933 Remote Similarity NPC238948
0.6933 Remote Similarity NPC215745
0.6923 Remote Similarity NPC322461
0.6914 Remote Similarity NPC44261
0.6912 Remote Similarity NPC159650
0.6912 Remote Similarity NPC302564
0.6912 Remote Similarity NPC22897
0.6912 Remote Similarity NPC222852
0.6905 Remote Similarity NPC26078
0.6905 Remote Similarity NPC473658
0.6901 Remote Similarity NPC478099
0.6901 Remote Similarity NPC470688
0.6901 Remote Similarity NPC470123
0.6901 Remote Similarity NPC476589
0.6901 Remote Similarity NPC478098
0.6901 Remote Similarity NPC19769
0.6892 Remote Similarity NPC476012
0.6892 Remote Similarity NPC64234
0.6892 Remote Similarity NPC37929
0.6885 Remote Similarity NPC128280
0.6885 Remote Similarity NPC308331
0.6875 Remote Similarity NPC151919
0.6866 Remote Similarity NPC472445
0.6866 Remote Similarity NPC283502
0.6857 Remote Similarity NPC155849
0.6857 Remote Similarity NPC132243
0.6857 Remote Similarity NPC322457
0.6849 Remote Similarity NPC63873
0.6842 Remote Similarity NPC476590
0.6842 Remote Similarity NPC114727
0.6835 Remote Similarity NPC469617
0.6835 Remote Similarity NPC271632
0.6833 Remote Similarity NPC6963
0.6833 Remote Similarity NPC304079
0.6829 Remote Similarity NPC161670
0.6829 Remote Similarity NPC196487
0.6829 Remote Similarity NPC475706
0.6829 Remote Similarity NPC14575
0.6825 Remote Similarity NPC27264
0.6825 Remote Similarity NPC236338
0.6825 Remote Similarity NPC15789
0.6824 Remote Similarity NPC307092
0.6824 Remote Similarity NPC51358
0.6812 Remote Similarity NPC476585
0.6806 Remote Similarity NPC308294
0.6806 Remote Similarity NPC142423
0.68 Remote Similarity NPC181587
0.68 Remote Similarity NPC133098
0.6795 Remote Similarity NPC471225
0.6795 Remote Similarity NPC475711
0.679 Remote Similarity NPC474439
0.679 Remote Similarity NPC313677
0.679 Remote Similarity NPC474028
0.6786 Remote Similarity NPC476079
0.6786 Remote Similarity NPC103743
0.6786 Remote Similarity NPC113370
0.6765 Remote Similarity NPC471619
0.6761 Remote Similarity NPC471611
0.6761 Remote Similarity NPC148233
0.6761 Remote Similarity NPC25747
0.6761 Remote Similarity NPC308457
0.6757 Remote Similarity NPC236208
0.6757 Remote Similarity NPC475982
0.6753 Remote Similarity NPC161038
0.6753 Remote Similarity NPC68624
0.675 Remote Similarity NPC160582
0.6747 Remote Similarity NPC307112
0.6721 Remote Similarity NPC270706
0.6716 Remote Similarity NPC325977
0.6712 Remote Similarity NPC225272
0.6712 Remote Similarity NPC478097
0.6712 Remote Similarity NPC203335
0.6711 Remote Similarity NPC185186
0.6711 Remote Similarity NPC287878
0.6711 Remote Similarity NPC327383
0.6711 Remote Similarity NPC329914
0.6709 Remote Similarity NPC473471
0.6709 Remote Similarity NPC108816
0.6709 Remote Similarity NPC267231
0.6709 Remote Similarity NPC93763

  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 NPC471566 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
0.75 Intermediate Similarity NPD4220 Pre-registration
0.7013 Intermediate Similarity NPD4756 Discovery
0.6719 Remote Similarity NPD6927 Phase 3
0.6571 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6479 Remote Similarity NPD4192 Approved
0.6479 Remote Similarity NPD4194 Approved
0.6479 Remote Similarity NPD4191 Approved
0.6479 Remote Similarity NPD4193 Approved
0.6452 Remote Similarity NPD4222 Approved
0.6267 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6235 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6216 Remote Similarity NPD2685 Clinical (unspecified phase)
0.619 Remote Similarity NPD39 Approved
0.618 Remote Similarity NPD7838 Discovery
0.6154 Remote Similarity NPD3173 Approved
0.6143 Remote Similarity NPD8779 Phase 3
0.6129 Remote Similarity NPD9411 Phase 1
0.6129 Remote Similarity NPD5326 Phase 3
0.6118 Remote Similarity NPD7154 Phase 3
0.6081 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6064 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6056 Remote Similarity NPD6109 Phase 1
0.6 Remote Similarity NPD5209 Approved
0.6 Remote Similarity NPD5343 Approved
0.5938 Remote Similarity NPD4265 Approved
0.5926 Remote Similarity NPD8039 Approved
0.5918 Remote Similarity NPD5909 Discontinued
0.5824 Remote Similarity NPD6698 Approved
0.5824 Remote Similarity NPD46 Approved
0.5797 Remote Similarity NPD3172 Approved
0.5781 Remote Similarity NPD6096 Approved
0.5781 Remote Similarity NPD6097 Approved
0.5765 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5761 Remote Similarity NPD7637 Suspended
0.5733 Remote Similarity NPD2664 Clinical (unspecified phase)
0.573 Remote Similarity NPD4249 Approved
0.5714 Remote Similarity NPD3196 Approved
0.5714 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3194 Approved
0.5714 Remote Similarity NPD4266 Approved
0.5714 Remote Similarity NPD3195 Phase 2
0.5699 Remote Similarity NPD5779 Approved
0.5699 Remote Similarity NPD5778 Approved
0.5692 Remote Similarity NPD3174 Discontinued
0.567 Remote Similarity NPD6648 Approved
0.5667 Remote Similarity NPD4250 Approved
0.5667 Remote Similarity NPD4251 Approved
0.5667 Remote Similarity NPD1282 Approved
0.5652 Remote Similarity NPD5785 Approved
0.5616 Remote Similarity NPD585 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