Structure

Physi-Chem Properties

Molecular Weight:  250.16
Volume:  263.425
LogP:  2.977
LogD:  3.054
LogS:  -2.921
# Rotatable Bonds:  0
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.621
Synthetic Accessibility Score:  4.254
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.655
MDCK Permeability:  3.660645234049298e-05
Pgp-inhibitor:  0.934
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.891
30% Bioavailability (F30%):  0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.356
Plasma Protein Binding (PPB):  78.20543670654297%
Volume Distribution (VD):  0.772
Pgp-substrate:  26.767316818237305%

ADMET: Metabolism

CYP1A2-inhibitor:  0.081
CYP1A2-substrate:  0.409
CYP2C19-inhibitor:  0.041
CYP2C19-substrate:  0.889
CYP2C9-inhibitor:  0.029
CYP2C9-substrate:  0.144
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.114
CYP3A4-inhibitor:  0.709
CYP3A4-substrate:  0.745

ADMET: Excretion

Clearance (CL):  15.272
Half-life (T1/2):  0.699

ADMET: Toxicity

hERG Blockers:  0.043
Human Hepatotoxicity (H-HT):  0.388
Drug-inuced Liver Injury (DILI):  0.822
AMES Toxicity:  0.069
Rat Oral Acute Toxicity:  0.212
Maximum Recommended Daily Dose:  0.177
Skin Sensitization:  0.51
Carcinogencity:  0.751
Eye Corrosion:  0.491
Eye Irritation:  0.559
Respiratory Toxicity:  0.902

Download Data

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

  Natural Product: NPC157518

Natural Product ID:  NPC157518
Common Name*:   2,3,11Beta,13-Tetrahydroaromaticin
IUPAC Name:   (1R,3aS,5R,5aS,8aS,9aR)-1,5,8a-trimethyl-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,7-b]furan-2,8-dione
Synonyms:   2,3,11Beta,13-Tetrahydroaromaticin
Standard InCHIKey:  SMONPNAHOSGWNR-QQTPGOFBSA-N
Standard InCHI:  InChI=1S/C15H22O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h8-12H,4-7H2,1-3H3/t8-,9-,10-,11+,12+,15+/m1/s1
SMILES:  C[C@@H]1C[C@H]2[C@H](C[C@@]3(C)[C@H]1CCC3=O)[C@@H](C)C(=O)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1912046
PubChem CID:   57398174
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0002046] Ambrosanolides and secoambrosanolides

*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
NPO22238 Inula falconeri Species Asteraceae Eukaryota aerial parts Tibet, China n.a. PMID[21924800]
NPO22238 Inula falconeri Species Asteraceae 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 10800.0 nM PMID[455892]

☑ 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 NPC157518 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
0.9091 High Similarity NPC470243
0.8696 High Similarity NPC179922
0.8286 Intermediate Similarity NPC215030
0.8108 Intermediate Similarity NPC290508
0.8108 Intermediate Similarity NPC293418
0.8108 Intermediate Similarity NPC73052
0.7971 Intermediate Similarity NPC5714
0.7792 Intermediate Similarity NPC54468
0.7778 Intermediate Similarity NPC477867
0.7742 Intermediate Similarity NPC319589
0.7703 Intermediate Similarity NPC208223
0.7667 Intermediate Similarity NPC305182
0.7632 Intermediate Similarity NPC51507
0.7632 Intermediate Similarity NPC6823
0.7541 Intermediate Similarity NPC314084
0.7534 Intermediate Similarity NPC469641
0.7534 Intermediate Similarity NPC469643
0.75 Intermediate Similarity NPC238593
0.7463 Intermediate Similarity NPC306750
0.7463 Intermediate Similarity NPC253204
0.7397 Intermediate Similarity NPC248567
0.7333 Intermediate Similarity NPC471046
0.7313 Intermediate Similarity NPC66145
0.7313 Intermediate Similarity NPC478126
0.7297 Intermediate Similarity NPC320537
0.7297 Intermediate Similarity NPC143979
0.726 Intermediate Similarity NPC197701
0.7229 Intermediate Similarity NPC12872
0.7229 Intermediate Similarity NPC168679
0.7215 Intermediate Similarity NPC212340
0.72 Intermediate Similarity NPC471491
0.7179 Intermediate Similarity NPC1882
0.7164 Intermediate Similarity NPC230070
0.7164 Intermediate Similarity NPC9880
0.7164 Intermediate Similarity NPC87828
0.7162 Intermediate Similarity NPC474755
0.716 Intermediate Similarity NPC161957
0.7083 Intermediate Similarity NPC119838
0.7073 Intermediate Similarity NPC236692
0.7073 Intermediate Similarity NPC70555
0.7073 Intermediate Similarity NPC309757
0.7073 Intermediate Similarity NPC104961
0.7073 Intermediate Similarity NPC70422
0.7059 Intermediate Similarity NPC191339
0.7059 Intermediate Similarity NPC286341
0.7037 Intermediate Similarity NPC291310
0.7013 Intermediate Similarity NPC15975
0.7013 Intermediate Similarity NPC143250
0.7013 Intermediate Similarity NPC195785
0.7 Intermediate Similarity NPC52700
0.7 Intermediate Similarity NPC63182
0.7 Intermediate Similarity NPC105329
0.7 Intermediate Similarity NPC145045
0.7 Intermediate Similarity NPC282440
0.6988 Remote Similarity NPC201658
0.6988 Remote Similarity NPC118601
0.6986 Remote Similarity NPC296522
0.6986 Remote Similarity NPC475062
0.6986 Remote Similarity NPC144511
0.6986 Remote Similarity NPC98711
0.6986 Remote Similarity NPC295788
0.6977 Remote Similarity NPC200237
0.6977 Remote Similarity NPC153590
0.6962 Remote Similarity NPC134227
0.6962 Remote Similarity NPC74673
0.6962 Remote Similarity NPC69271
0.6962 Remote Similarity NPC156658
0.6962 Remote Similarity NPC258965
0.6957 Remote Similarity NPC83088
0.6933 Remote Similarity NPC474100
0.6933 Remote Similarity NPC51249
0.6933 Remote Similarity NPC475260
0.6933 Remote Similarity NPC475232
0.6933 Remote Similarity NPC109510
0.6933 Remote Similarity NPC473775
0.6933 Remote Similarity NPC473699
0.6914 Remote Similarity NPC215294
0.6914 Remote Similarity NPC157328
0.6914 Remote Similarity NPC39588
0.6905 Remote Similarity NPC178875
0.6905 Remote Similarity NPC53158
0.6901 Remote Similarity NPC215987
0.6901 Remote Similarity NPC306805
0.6897 Remote Similarity NPC470424
0.6883 Remote Similarity NPC226242
0.6875 Remote Similarity NPC126248
0.6875 Remote Similarity NPC47635
0.6875 Remote Similarity NPC35089
0.6875 Remote Similarity NPC58631
0.6875 Remote Similarity NPC10276
0.6867 Remote Similarity NPC56593
0.6849 Remote Similarity NPC319007
0.6842 Remote Similarity NPC55508
0.6835 Remote Similarity NPC469690
0.6835 Remote Similarity NPC182550
0.6835 Remote Similarity NPC469620
0.6833 Remote Similarity NPC273545
0.6824 Remote Similarity NPC200580
0.6824 Remote Similarity NPC117405
0.6824 Remote Similarity NPC52198
0.6806 Remote Similarity NPC84562
0.68 Remote Similarity NPC478227
0.6795 Remote Similarity NPC122264
0.6795 Remote Similarity NPC471151
0.6795 Remote Similarity NPC169389
0.679 Remote Similarity NPC13494
0.679 Remote Similarity NPC246076
0.679 Remote Similarity NPC148740
0.679 Remote Similarity NPC102156
0.6786 Remote Similarity NPC24728
0.6786 Remote Similarity NPC270270
0.6782 Remote Similarity NPC473273
0.6782 Remote Similarity NPC473263
0.6782 Remote Similarity NPC60386
0.6782 Remote Similarity NPC473234
0.6782 Remote Similarity NPC308656
0.6761 Remote Similarity NPC314103
0.6757 Remote Similarity NPC178541
0.6753 Remote Similarity NPC132064
0.675 Remote Similarity NPC125366
0.675 Remote Similarity NPC276356
0.675 Remote Similarity NPC170038
0.6747 Remote Similarity NPC473350
0.6747 Remote Similarity NPC33570
0.6747 Remote Similarity NPC21471
0.6744 Remote Similarity NPC253144
0.6742 Remote Similarity NPC91771
0.6742 Remote Similarity NPC142529
0.6742 Remote Similarity NPC126156
0.6712 Remote Similarity NPC469868
0.6709 Remote Similarity NPC185465
0.6707 Remote Similarity NPC128246
0.6707 Remote Similarity NPC472847
0.6707 Remote Similarity NPC111409
0.6707 Remote Similarity NPC245665
0.6706 Remote Similarity NPC471149
0.6706 Remote Similarity NPC470009
0.6705 Remote Similarity NPC473331
0.6667 Remote Similarity NPC123177
0.6667 Remote Similarity NPC18543
0.6667 Remote Similarity NPC472959
0.6667 Remote Similarity NPC476330
0.6667 Remote Similarity NPC284185
0.6667 Remote Similarity NPC150978
0.6667 Remote Similarity NPC472955
0.6667 Remote Similarity NPC92489
0.6667 Remote Similarity NPC39411
0.6667 Remote Similarity NPC295256
0.6667 Remote Similarity NPC255580
0.6667 Remote Similarity NPC74103
0.6667 Remote Similarity NPC92139
0.6667 Remote Similarity NPC70595
0.6628 Remote Similarity NPC155935
0.6628 Remote Similarity NPC283409
0.6628 Remote Similarity NPC32922
0.6627 Remote Similarity NPC101138
0.6627 Remote Similarity NPC82492
0.6627 Remote Similarity NPC25802
0.6627 Remote Similarity NPC100391
0.6627 Remote Similarity NPC109512
0.6627 Remote Similarity NPC51135
0.6625 Remote Similarity NPC474754
0.6625 Remote Similarity NPC320144
0.6625 Remote Similarity NPC472310
0.6625 Remote Similarity NPC118987
0.6623 Remote Similarity NPC472966
0.6622 Remote Similarity NPC82315
0.6613 Remote Similarity NPC326957
0.6591 Remote Similarity NPC472238
0.6591 Remote Similarity NPC472237
0.6588 Remote Similarity NPC475773
0.6588 Remote Similarity NPC239938
0.6585 Remote Similarity NPC164289
0.6585 Remote Similarity NPC289486
0.6585 Remote Similarity NPC100366
0.6585 Remote Similarity NPC242771
0.6585 Remote Similarity NPC311642
0.6585 Remote Similarity NPC61107
0.6582 Remote Similarity NPC475932
0.6582 Remote Similarity NPC307865
0.6582 Remote Similarity NPC214030
0.6582 Remote Similarity NPC83108
0.6582 Remote Similarity NPC474404
0.6582 Remote Similarity NPC70996
0.6582 Remote Similarity NPC477918
0.6579 Remote Similarity NPC469940
0.6579 Remote Similarity NPC40327
0.6575 Remote Similarity NPC135043
0.6575 Remote Similarity NPC315525
0.6552 Remote Similarity NPC54065
0.6552 Remote Similarity NPC297474
0.6552 Remote Similarity NPC35809
0.6548 Remote Similarity NPC204105
0.6548 Remote Similarity NPC284534
0.6548 Remote Similarity NPC300082
0.6548 Remote Similarity NPC470223
0.6543 Remote Similarity NPC302426
0.6538 Remote Similarity NPC21220
0.6538 Remote Similarity NPC155441
0.6538 Remote Similarity NPC179858

  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 NPC157518 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
0.726 Intermediate Similarity NPD5777 Approved
0.7083 Intermediate Similarity NPD229 Approved
0.6912 Remote Similarity NPD3198 Approved
0.6753 Remote Similarity NPD3702 Approved
0.6667 Remote Similarity NPD9496 Clinical (unspecified phase)
0.65 Remote Similarity NPD387 Clinical (unspecified phase)
0.65 Remote Similarity NPD4238 Approved
0.65 Remote Similarity NPD4802 Phase 2
0.6444 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6438 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6418 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6418 Remote Similarity NPD615 Clinical (unspecified phase)
0.641 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6351 Remote Similarity NPD4224 Phase 2
0.6349 Remote Similarity NPD343 Approved
0.6349 Remote Similarity NPD344 Approved
0.6349 Remote Similarity NPD345 Approved
0.6329 Remote Similarity NPD3703 Phase 2
0.6316 Remote Similarity NPD3698 Phase 2
0.6316 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6316 Remote Similarity NPD3700 Clinical (unspecified phase)
0.629 Remote Similarity NPD2699 Approved
0.625 Remote Similarity NPD6117 Approved
0.6234 Remote Similarity NPD4244 Approved
0.6234 Remote Similarity NPD4245 Approved
0.619 Remote Similarity NPD634 Phase 3
0.619 Remote Similarity NPD6435 Approved
0.6173 Remote Similarity NPD6116 Phase 1
0.6163 Remote Similarity NPD1694 Approved
0.6154 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6081 Approved
0.6136 Remote Similarity NPD6903 Approved
0.6098 Remote Similarity NPD6114 Approved
0.6098 Remote Similarity NPD6118 Approved
0.6098 Remote Similarity NPD6115 Approved
0.6098 Remote Similarity NPD6697 Approved
0.6092 Remote Similarity NPD7521 Approved
0.6092 Remote Similarity NPD7334 Approved
0.6092 Remote Similarity NPD5330 Approved
0.6092 Remote Similarity NPD6684 Approved
0.6092 Remote Similarity NPD7146 Approved
0.6092 Remote Similarity NPD6409 Approved
0.6081 Remote Similarity NPD7909 Approved
0.6067 Remote Similarity NPD1695 Approved
0.6026 Remote Similarity NPD4789 Approved
0.6 Remote Similarity NPD2266 Phase 2
0.5955 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5952 Remote Similarity NPD5368 Approved
0.5938 Remote Similarity NPD1700 Approved
0.5921 Remote Similarity NPD375 Phase 2
0.5909 Remote Similarity NPD5786 Approved
0.5904 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5897 Remote Similarity NPD3726 Approved
0.5897 Remote Similarity NPD3725 Approved
0.5882 Remote Similarity NPD5369 Approved
0.587 Remote Similarity NPD6399 Phase 3
0.5859 Remote Similarity NPD6008 Approved
0.5824 Remote Similarity NPD5207 Approved
0.5778 Remote Similarity NPD6672 Approved
0.5778 Remote Similarity NPD5737 Approved
0.5769 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5769 Remote Similarity NPD5360 Phase 3
0.5761 Remote Similarity NPD8034 Phase 2
0.5761 Remote Similarity NPD8035 Phase 2
0.5758 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5758 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5758 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5745 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3671 Phase 1
0.5698 Remote Similarity NPD1779 Approved
0.5698 Remote Similarity NPD1780 Approved
0.5667 Remote Similarity NPD9449 Clinical (unspecified phase)
0.5652 Remote Similarity NPD5785 Approved
0.5652 Remote Similarity NPD3186 Phase 1
0.5638 Remote Similarity NPD6001 Approved
0.5632 Remote Similarity NPD4270 Approved
0.5632 Remote Similarity NPD4269 Approved
0.5618 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5618 Remote Similarity NPD7520 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