Structure

Physi-Chem Properties

Molecular Weight:  364.26
Volume:  399.207
LogP:  3.635
LogD:  2.739
LogS:  -4.219
# Rotatable Bonds:  6
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.568
Synthetic Accessibility Score:  4.853
Fsp3:  0.773
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.61
MDCK Permeability:  1.998951302084606e-05
Pgp-inhibitor:  0.991
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.032
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.599
Plasma Protein Binding (PPB):  88.41178131103516%
Volume Distribution (VD):  1.436
Pgp-substrate:  12.862298011779785%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.359
CYP2C19-inhibitor:  0.153
CYP2C19-substrate:  0.866
CYP2C9-inhibitor:  0.181
CYP2C9-substrate:  0.401
CYP2D6-inhibitor:  0.033
CYP2D6-substrate:  0.076
CYP3A4-inhibitor:  0.888
CYP3A4-substrate:  0.434

ADMET: Excretion

Clearance (CL):  3.436
Half-life (T1/2):  0.084

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.209
Drug-inuced Liver Injury (DILI):  0.63
AMES Toxicity:  0.023
Rat Oral Acute Toxicity:  0.095
Maximum Recommended Daily Dose:  0.033
Skin Sensitization:  0.07
Carcinogencity:  0.345
Eye Corrosion:  0.037
Eye Irritation:  0.117
Respiratory Toxicity:  0.918

Download Data

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

  Natural Product: NPC209431

Natural Product ID:  NPC209431
Common Name*:   (4S)-4-Prop-1-En-2-Ylcyclohexene-1-Carbaldehyde
IUPAC Name:   (4S)-4-prop-1-en-2-ylcyclohexene-1-carbaldehyde
Synonyms:   S(-)-Perillaldehyde
Standard InCHIKey:  RUMOYJJNUMEFDD-SNVBAGLBSA-N
Standard InCHI:  InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m1/s1
SMILES:  O=CC1=CC[C@H](CC1)C(=C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL442913
PubChem CID:   2724159
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001401] Menthane monoterpenoids

*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
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota fruits n.a. n.a. PMID[16038540]
NPO14358 Rhodobacter sphaeroides Species Rhodobacteraceae Bacteria n.a. n.a. n.a. PMID[1612412]
NPO8068 Blumea mollis Species Asteraceae Eukaryota n.a. leaf n.a. PMID[18566831]
NPO14162 Chlorophytum borivilianum Species Asparagaceae Eukaryota roots n.a. n.a. PMID[19128156]
NPO7016 Gardenia tubifera Species Rubiaceae Eukaryota exudate n.a. n.a. PMID[20028108]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20674349]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. stem n.a. PMID[21428274]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[21428274]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[22272932]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25320841]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. fruit n.a. PMID[26169681]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16703 Isodon lophanthoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4004 Aquilegia ecalcarata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO746 Panax innovans Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13968 Garcinia scortechinii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12357 Lycopus europaeus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13766 Ceanothus velutinus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10550 Artemisia hanseniana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3465 Aconitum leucostomum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5191 Penicillium cinerascens Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13467 Anarsia lineatella Species Gelechiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14162 Chlorophytum borivilianum Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12509 Dipterocarpus dyeri Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4004 Aquilegia ecalcarata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1795 Fragaria vesca Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4671 Persea mexicana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13014 Ipomoea cairica Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14057 Apollonias barbujana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7016 Gardenia tubifera Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16703 Isodon lophanthoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO205 Lasianthus fordii Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11492 Kopsia grandifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8068 Blumea mollis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8892 Sordaria araneosa Species Sordariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14358 Rhodobacter sphaeroides Species Rhodobacteraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11998 Ledebouria socialis Species Hyacinthaceae 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
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 138 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54941 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48557.7 nM PubChem BioAssay data set

☑ 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 NPC209431 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 NPC100809
0.8462 Intermediate Similarity NPC176819
0.8462 Intermediate Similarity NPC163984
0.8462 Intermediate Similarity NPC58970
0.8364 Intermediate Similarity NPC188789
0.8235 Intermediate Similarity NPC276009
0.8235 Intermediate Similarity NPC195246
0.8235 Intermediate Similarity NPC22098
0.8113 Intermediate Similarity NPC32351
0.8077 Intermediate Similarity NPC91962
0.8065 Intermediate Similarity NPC4370
0.8065 Intermediate Similarity NPC290350
0.8 Intermediate Similarity NPC268564
0.7963 Intermediate Similarity NPC234829
0.7857 Intermediate Similarity NPC250539
0.7843 Intermediate Similarity NPC114841
0.7656 Intermediate Similarity NPC155198
0.7647 Intermediate Similarity NPC106819
0.7636 Intermediate Similarity NPC30433
0.7636 Intermediate Similarity NPC64866
0.7576 Intermediate Similarity NPC304983
0.7576 Intermediate Similarity NPC474562
0.75 Intermediate Similarity NPC276764
0.75 Intermediate Similarity NPC25771
0.75 Intermediate Similarity NPC22182
0.75 Intermediate Similarity NPC472304
0.7419 Intermediate Similarity NPC165695
0.7407 Intermediate Similarity NPC324812
0.74 Intermediate Similarity NPC101147
0.7358 Intermediate Similarity NPC166788
0.7353 Intermediate Similarity NPC211641
0.7353 Intermediate Similarity NPC128346
0.7353 Intermediate Similarity NPC219232
0.7333 Intermediate Similarity NPC56905
0.7333 Intermediate Similarity NPC27610
0.7333 Intermediate Similarity NPC308108
0.7333 Intermediate Similarity NPC311852
0.7333 Intermediate Similarity NPC170799
0.7308 Intermediate Similarity NPC292463
0.7288 Intermediate Similarity NPC473733
0.7241 Intermediate Similarity NPC95581
0.7231 Intermediate Similarity NPC193770
0.7222 Intermediate Similarity NPC236355
0.7222 Intermediate Similarity NPC14917
0.7222 Intermediate Similarity NPC4079
0.7193 Intermediate Similarity NPC471751
0.7188 Intermediate Similarity NPC470329
0.7188 Intermediate Similarity NPC251118
0.7167 Intermediate Similarity NPC115385
0.7167 Intermediate Similarity NPC281986
0.7167 Intermediate Similarity NPC208749
0.7167 Intermediate Similarity NPC22019
0.7167 Intermediate Similarity NPC321568
0.7143 Intermediate Similarity NPC19907
0.7119 Intermediate Similarity NPC275472
0.7097 Intermediate Similarity NPC127582
0.7077 Intermediate Similarity NPC166791
0.7077 Intermediate Similarity NPC100719
0.7077 Intermediate Similarity NPC322035
0.7069 Intermediate Similarity NPC474141
0.7069 Intermediate Similarity NPC23117
0.7069 Intermediate Similarity NPC37644
0.7059 Intermediate Similarity NPC18205
0.7059 Intermediate Similarity NPC12319
0.7037 Intermediate Similarity NPC239754
0.7031 Intermediate Similarity NPC6697
0.7031 Intermediate Similarity NPC169275
0.7031 Intermediate Similarity NPC475124
0.7031 Intermediate Similarity NPC150162
0.7031 Intermediate Similarity NPC285371
0.7031 Intermediate Similarity NPC52449
0.7031 Intermediate Similarity NPC212210
0.7015 Intermediate Similarity NPC61702
0.7015 Intermediate Similarity NPC261398
0.7015 Intermediate Similarity NPC162867
0.6984 Remote Similarity NPC213152
0.6964 Remote Similarity NPC145311
0.6949 Remote Similarity NPC5626
0.6944 Remote Similarity NPC115515
0.6944 Remote Similarity NPC253561
0.6944 Remote Similarity NPC80088
0.6935 Remote Similarity NPC285594
0.6935 Remote Similarity NPC96551
0.6923 Remote Similarity NPC33489
0.6923 Remote Similarity NPC268039
0.6909 Remote Similarity NPC163751
0.6909 Remote Similarity NPC262558
0.6909 Remote Similarity NPC110234
0.6909 Remote Similarity NPC8610
0.6909 Remote Similarity NPC44363
0.6901 Remote Similarity NPC469796
0.6901 Remote Similarity NPC469793
0.6885 Remote Similarity NPC193695
0.6875 Remote Similarity NPC32285
0.6875 Remote Similarity NPC288253
0.6866 Remote Similarity NPC87141
0.6866 Remote Similarity NPC260474
0.6866 Remote Similarity NPC188292
0.6866 Remote Similarity NPC310992
0.6863 Remote Similarity NPC33761
0.6849 Remote Similarity NPC90965
0.6849 Remote Similarity NPC170793
0.6842 Remote Similarity NPC228776
0.6825 Remote Similarity NPC25853
0.68 Remote Similarity NPC254764
0.6792 Remote Similarity NPC287397
0.6792 Remote Similarity NPC67920
0.6792 Remote Similarity NPC298710
0.678 Remote Similarity NPC14002
0.678 Remote Similarity NPC45283
0.6774 Remote Similarity NPC94991
0.6774 Remote Similarity NPC266295
0.6774 Remote Similarity NPC30215
0.6765 Remote Similarity NPC256846
0.6757 Remote Similarity NPC474509
0.6757 Remote Similarity NPC472301
0.6727 Remote Similarity NPC191337
0.6724 Remote Similarity NPC27438
0.6721 Remote Similarity NPC20603
0.6719 Remote Similarity NPC97322
0.6716 Remote Similarity NPC475523
0.6712 Remote Similarity NPC228911
0.6667 Remote Similarity NPC143834
0.6667 Remote Similarity NPC259261
0.6667 Remote Similarity NPC2634
0.6667 Remote Similarity NPC477789
0.6667 Remote Similarity NPC183422
0.6667 Remote Similarity NPC242722
0.6667 Remote Similarity NPC251929
0.6667 Remote Similarity NPC265782
0.6667 Remote Similarity NPC202850
0.6667 Remote Similarity NPC119229
0.6667 Remote Similarity NPC63396
0.6615 Remote Similarity NPC167256
0.661 Remote Similarity NPC216407
0.6607 Remote Similarity NPC471752
0.6579 Remote Similarity NPC470813
0.6575 Remote Similarity NPC471061
0.6571 Remote Similarity NPC54123
0.6552 Remote Similarity NPC118788
0.6552 Remote Similarity NPC15325
0.6552 Remote Similarity NPC116906
0.6545 Remote Similarity NPC477686
0.6528 Remote Similarity NPC472256
0.6522 Remote Similarity NPC474060
0.6522 Remote Similarity NPC469914
0.6522 Remote Similarity NPC139397
0.6515 Remote Similarity NPC469662
0.65 Remote Similarity NPC296311
0.6494 Remote Similarity NPC307258
0.6486 Remote Similarity NPC59436
0.6481 Remote Similarity NPC208936
0.6479 Remote Similarity NPC470045
0.6479 Remote Similarity NPC303613
0.6479 Remote Similarity NPC470044
0.6479 Remote Similarity NPC474228
0.6479 Remote Similarity NPC251705
0.6471 Remote Similarity NPC472875
0.6471 Remote Similarity NPC269985
0.6471 Remote Similarity NPC76145
0.6471 Remote Similarity NPC34764
0.6471 Remote Similarity NPC190810
0.6471 Remote Similarity NPC279300
0.6462 Remote Similarity NPC60565
0.6462 Remote Similarity NPC269737
0.6462 Remote Similarity NPC475795
0.6441 Remote Similarity NPC244038
0.6438 Remote Similarity NPC40353
0.6438 Remote Similarity NPC472959
0.6438 Remote Similarity NPC215481
0.6438 Remote Similarity NPC470525
0.6429 Remote Similarity NPC307176
0.6429 Remote Similarity NPC260040
0.6429 Remote Similarity NPC159577
0.6429 Remote Similarity NPC282593
0.6429 Remote Similarity NPC35734
0.6418 Remote Similarity NPC474304
0.6418 Remote Similarity NPC474329
0.6415 Remote Similarity NPC48930
0.6415 Remote Similarity NPC113082
0.6415 Remote Similarity NPC323278
0.6415 Remote Similarity NPC111474
0.641 Remote Similarity NPC470812
0.6406 Remote Similarity NPC473494
0.6364 Remote Similarity NPC151728
0.6364 Remote Similarity NPC57463
0.6364 Remote Similarity NPC197238
0.6364 Remote Similarity NPC142683
0.6364 Remote Similarity NPC301972
0.6364 Remote Similarity NPC202118
0.6351 Remote Similarity NPC187568
0.6351 Remote Similarity NPC329318
0.6351 Remote Similarity NPC197659
0.6351 Remote Similarity NPC41780
0.6349 Remote Similarity NPC192427
0.6349 Remote Similarity NPC55004
0.6349 Remote Similarity NPC267626
0.6349 Remote Similarity NPC49575
0.6349 Remote Similarity NPC230823
0.6346 Remote Similarity NPC297643

  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 NPC209431 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
0.7333 Intermediate Similarity NPD287 Approved
0.6667 Remote Similarity NPD4691 Approved
0.6522 Remote Similarity NPD4137 Phase 3
0.6471 Remote Similarity NPD319 Phase 1
0.6429 Remote Similarity NPD4747 Approved
0.6389 Remote Similarity NPD4058 Approved
0.6324 Remote Similarity NPD7331 Phase 2
0.629 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6164 Remote Similarity NPD5733 Approved
0.6164 Remote Similarity NPD4687 Approved
0.6143 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6111 Remote Similarity NPD5276 Approved
0.6087 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6032 Remote Similarity NPD342 Phase 1
0.5942 Remote Similarity NPD7341 Phase 2
0.5882 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5802 Remote Similarity NPD3133 Approved
0.5802 Remote Similarity NPD3666 Approved
0.5802 Remote Similarity NPD3665 Phase 1
0.575 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5732 Remote Similarity NPD1694 Approved
0.5696 Remote Similarity NPD4695 Discontinued
0.5679 Remote Similarity NPD3527 Clinical (unspecified phase)
0.5663 Remote Similarity NPD7521 Approved
0.5663 Remote Similarity NPD7334 Approved
0.5663 Remote Similarity NPD6684 Approved
0.5663 Remote Similarity NPD3618 Phase 1
0.5663 Remote Similarity NPD6409 Approved
0.5663 Remote Similarity NPD7146 Approved
0.5663 Remote Similarity NPD5330 Approved
0.5658 Remote Similarity NPD8039 Approved
0.5636 Remote Similarity NPD5783 Phase 3
0.5625 Remote Similarity NPD8028 Phase 2

  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