Structure

Physi-Chem Properties

Molecular Weight:  414.24
Volume:  449.339
LogP:  3.864
LogD:  1.713
LogS:  -3.499
# Rotatable Bonds:  8
TPSA:  94.83
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.447
Synthetic Accessibility Score:  4.615
Fsp3:  0.52
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:  -5.152
MDCK Permeability:  5.721654360968387e-06
Pgp-inhibitor:  0.106
Pgp-substrate:  0.953
Human Intestinal Absorption (HIA):  0.251
20% Bioavailability (F20%):  0.15
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.186
Plasma Protein Binding (PPB):  97.30977630615234%
Volume Distribution (VD):  0.418
Pgp-substrate:  1.3141816854476929%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.107
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.603
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.577
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.117
CYP3A4-inhibitor:  0.063
CYP3A4-substrate:  0.418

ADMET: Excretion

Clearance (CL):  2.186
Half-life (T1/2):  0.933

ADMET: Toxicity

hERG Blockers:  0.056
Human Hepatotoxicity (H-HT):  0.62
Drug-inuced Liver Injury (DILI):  0.958
AMES Toxicity:  0.061
Rat Oral Acute Toxicity:  0.252
Maximum Recommended Daily Dose:  0.854
Skin Sensitization:  0.361
Carcinogencity:  0.114
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.953

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

  Natural Product: NPC229612

Natural Product ID:  NPC229612
Common Name*:   (2E,4Z,6E)-7-((1R,4As,6S,7R,8R,8Ar)-7-Hydroxy-2-(3-Hydroxy-2-Oxopropylidene)-3,6,8-Trimethyl-1,2,4A,5,6,7,8,8A-Octahydronaphthalen-1-Yl)-4,6-Dimethylhepta-2,4,6-Trienoic Acid
IUPAC Name:   (2E,4Z,6E)-7-[(1R,2E,4aS,6S,7R,8R,8aR)-7-hydroxy-2-(3-hydroxy-2-oxopropylidene)-3,6,8-trimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-1-yl]-4,6-dimethylhepta-2,4,6-trienoic acid
Synonyms:  
Standard InCHIKey:  OQJAHXQKGGHDPO-JUFDTIFTSA-N
Standard InCHI:  InChI=1S/C25H34O5/c1-14(6-7-23(28)29)8-15(2)9-22-21(12-20(27)13-26)16(3)10-19-11-17(4)25(30)18(5)24(19)22/h6-10,12,17-19,22,24-26,30H,11,13H2,1-5H3,(H,28,29)/b7-6+,14-8-,15-9+,21-12-/t17-,18+,19-,22+,24+,25+/m0/s1
SMILES:  C/C(=C/C(=C/[C@@H]1/C(=CC(=O)CO)/C(=C[C@H]2C[C@H](C)[C@H]([C@H](C)[C@@H]12)O)C)/C)/C=C/C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL490524
PubChem CID:   10669484
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001564] Bicyclic 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
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10479323]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12350167]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[14640527]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota Axinella verrucosa Mediterranean n.a. PMID[14738391]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15043411]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Sussex Inlet, New South Wales, Australia n.a. PMID[15104517]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15332862]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Berkeley Pit lake n.a. PMID[17970594]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. New Zealand n.a. PMID[19323568]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19326880]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20452770]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. North Sea n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Limonium tubiflorum n.a. PMID[21146414]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21916432]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22148349]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22458669]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23360521]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23477451]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23603293]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23972215]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24437979]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31433188]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9392888]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]

☑ 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
NPT638 Organism Sclerotinia sclerotiorum Sclerotinia sclerotiorum IZ = 16.0 mm PMID[558140]

☑ 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 NPC229612 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 NPC7280
0.9512 High Similarity NPC302360
0.939 High Similarity NPC57370
0.9167 High Similarity NPC109528
0.881 High Similarity NPC224455
0.8539 High Similarity NPC314727
0.8495 Intermediate Similarity NPC99726
0.8488 Intermediate Similarity NPC79945
0.8471 Intermediate Similarity NPC159148
0.8462 Intermediate Similarity NPC214697
0.8387 Intermediate Similarity NPC250757
0.8387 Intermediate Similarity NPC301534
0.8372 Intermediate Similarity NPC256112
0.8372 Intermediate Similarity NPC2524
0.8353 Intermediate Similarity NPC281880
0.8352 Intermediate Similarity NPC212948
0.8298 Intermediate Similarity NPC141401
0.8202 Intermediate Similarity NPC175145
0.8202 Intermediate Similarity NPC475069
0.8191 Intermediate Similarity NPC190713
0.8172 Intermediate Similarity NPC119562
0.8172 Intermediate Similarity NPC279410
0.8132 Intermediate Similarity NPC118011
0.8132 Intermediate Similarity NPC262858
0.8132 Intermediate Similarity NPC36668
0.8132 Intermediate Similarity NPC146554
0.8132 Intermediate Similarity NPC16265
0.8132 Intermediate Similarity NPC472240
0.8125 Intermediate Similarity NPC266955
0.8068 Intermediate Similarity NPC476927
0.8065 Intermediate Similarity NPC205034
0.8065 Intermediate Similarity NPC162615
0.8065 Intermediate Similarity NPC152778
0.8046 Intermediate Similarity NPC170303
0.8043 Intermediate Similarity NPC310479
0.8043 Intermediate Similarity NPC182136
0.8043 Intermediate Similarity NPC78973
0.8041 Intermediate Similarity NPC115899
0.8041 Intermediate Similarity NPC282524
0.8022 Intermediate Similarity NPC104560
0.8021 Intermediate Similarity NPC108368
0.8021 Intermediate Similarity NPC478056
0.8021 Intermediate Similarity NPC57079
0.8 Intermediate Similarity NPC16967
0.8 Intermediate Similarity NPC473153
0.8 Intermediate Similarity NPC473226
0.7979 Intermediate Similarity NPC191521
0.7979 Intermediate Similarity NPC474690
0.7979 Intermediate Similarity NPC299100
0.7979 Intermediate Similarity NPC476186
0.7938 Intermediate Similarity NPC327431
0.7935 Intermediate Similarity NPC472983
0.7917 Intermediate Similarity NPC208094
0.7912 Intermediate Similarity NPC245004
0.7912 Intermediate Similarity NPC473097
0.7895 Intermediate Similarity NPC180950
0.7889 Intermediate Similarity NPC35933
0.7882 Intermediate Similarity NPC265588
0.7879 Intermediate Similarity NPC475050
0.7872 Intermediate Similarity NPC476304
0.7872 Intermediate Similarity NPC38232
0.7865 Intermediate Similarity NPC474789
0.7865 Intermediate Similarity NPC52108
0.7857 Intermediate Similarity NPC115862
0.7849 Intermediate Similarity NPC221111
0.7849 Intermediate Similarity NPC280149
0.7841 Intermediate Similarity NPC6663
0.7841 Intermediate Similarity NPC142163
0.7835 Intermediate Similarity NPC471717
0.7835 Intermediate Similarity NPC92275
0.7835 Intermediate Similarity NPC166745
0.7835 Intermediate Similarity NPC235464
0.7826 Intermediate Similarity NPC473229
0.7822 Intermediate Similarity NPC472925
0.7802 Intermediate Similarity NPC82979
0.7791 Intermediate Similarity NPC132542
0.7791 Intermediate Similarity NPC91594
0.7789 Intermediate Similarity NPC469406
0.7789 Intermediate Similarity NPC469491
0.7789 Intermediate Similarity NPC470255
0.7778 Intermediate Similarity NPC155332
0.7778 Intermediate Similarity NPC32577
0.7778 Intermediate Similarity NPC114540
0.7778 Intermediate Similarity NPC306951
0.7766 Intermediate Similarity NPC74296
0.7766 Intermediate Similarity NPC110923
0.7766 Intermediate Similarity NPC142838
0.7745 Intermediate Similarity NPC295244
0.7745 Intermediate Similarity NPC470024
0.7742 Intermediate Similarity NPC246028
0.7742 Intermediate Similarity NPC20946
0.7738 Intermediate Similarity NPC265485
0.7738 Intermediate Similarity NPC220939
0.7732 Intermediate Similarity NPC474938
0.7732 Intermediate Similarity NPC108078
0.7732 Intermediate Similarity NPC253826
0.7732 Intermediate Similarity NPC320306
0.7732 Intermediate Similarity NPC474785
0.7727 Intermediate Similarity NPC271104
0.7723 Intermediate Similarity NPC172867
0.7717 Intermediate Similarity NPC131329
0.7717 Intermediate Similarity NPC181327
0.7708 Intermediate Similarity NPC476245
0.7708 Intermediate Similarity NPC295347
0.7708 Intermediate Similarity NPC88310
0.7701 Intermediate Similarity NPC172066
0.77 Intermediate Similarity NPC72151
0.77 Intermediate Similarity NPC95899
0.77 Intermediate Similarity NPC85742
0.7684 Intermediate Similarity NPC53555
0.7677 Intermediate Similarity NPC476240
0.7677 Intermediate Similarity NPC224720
0.7677 Intermediate Similarity NPC476223
0.7677 Intermediate Similarity NPC302537
0.7677 Intermediate Similarity NPC163372
0.7674 Intermediate Similarity NPC250621
0.7667 Intermediate Similarity NPC297398
0.766 Intermediate Similarity NPC19771
0.7653 Intermediate Similarity NPC218107
0.7653 Intermediate Similarity NPC316598
0.7653 Intermediate Similarity NPC103051
0.7653 Intermediate Similarity NPC474440
0.7647 Intermediate Similarity NPC109376
0.7647 Intermediate Similarity NPC473284
0.764 Intermediate Similarity NPC112868
0.764 Intermediate Similarity NPC476646
0.764 Intermediate Similarity NPC473420
0.7634 Intermediate Similarity NPC291665
0.7634 Intermediate Similarity NPC48107
0.7629 Intermediate Similarity NPC96859
0.7629 Intermediate Similarity NPC456
0.7629 Intermediate Similarity NPC195366
0.7629 Intermediate Similarity NPC305483
0.7629 Intermediate Similarity NPC472941
0.7629 Intermediate Similarity NPC114743
0.7629 Intermediate Similarity NPC471153
0.7629 Intermediate Similarity NPC328162
0.7624 Intermediate Similarity NPC118911
0.7619 Intermediate Similarity NPC95863
0.7619 Intermediate Similarity NPC23954
0.7614 Intermediate Similarity NPC100906
0.7614 Intermediate Similarity NPC242767
0.7609 Intermediate Similarity NPC472974
0.7609 Intermediate Similarity NPC474970
0.7609 Intermediate Similarity NPC131813
0.7609 Intermediate Similarity NPC202394
0.7609 Intermediate Similarity NPC322159
0.7604 Intermediate Similarity NPC474922
0.7604 Intermediate Similarity NPC474882
0.7604 Intermediate Similarity NPC23170
0.7604 Intermediate Similarity NPC80365
0.7604 Intermediate Similarity NPC474328
0.7604 Intermediate Similarity NPC472976
0.7604 Intermediate Similarity NPC38830
0.7604 Intermediate Similarity NPC472977
0.7604 Intermediate Similarity NPC57117
0.76 Intermediate Similarity NPC11956
0.76 Intermediate Similarity NPC136289
0.76 Intermediate Similarity NPC293753
0.76 Intermediate Similarity NPC308726
0.76 Intermediate Similarity NPC320447
0.76 Intermediate Similarity NPC119601
0.7586 Intermediate Similarity NPC283619
0.7586 Intermediate Similarity NPC203403
0.7586 Intermediate Similarity NPC85105
0.7586 Intermediate Similarity NPC149550
0.7582 Intermediate Similarity NPC53385
0.7582 Intermediate Similarity NPC231310
0.7582 Intermediate Similarity NPC33913
0.7582 Intermediate Similarity NPC238485
0.7582 Intermediate Similarity NPC102048
0.7579 Intermediate Similarity NPC301244
0.7579 Intermediate Similarity NPC472978
0.7579 Intermediate Similarity NPC329842
0.7579 Intermediate Similarity NPC233455
0.7579 Intermediate Similarity NPC477574
0.7579 Intermediate Similarity NPC474018
0.7579 Intermediate Similarity NPC72845
0.7579 Intermediate Similarity NPC65120
0.7579 Intermediate Similarity NPC4036
0.7579 Intermediate Similarity NPC158030
0.7579 Intermediate Similarity NPC473986
0.7579 Intermediate Similarity NPC474525
0.7579 Intermediate Similarity NPC145067
0.7579 Intermediate Similarity NPC472811
0.7576 Intermediate Similarity NPC476274
0.7573 Intermediate Similarity NPC224660
0.7558 Intermediate Similarity NPC69383
0.7558 Intermediate Similarity NPC171148
0.7558 Intermediate Similarity NPC313179
0.7556 Intermediate Similarity NPC202389
0.7556 Intermediate Similarity NPC471218
0.7553 Intermediate Similarity NPC50488
0.7553 Intermediate Similarity NPC474396
0.7553 Intermediate Similarity NPC82876
0.7553 Intermediate Similarity NPC257485
0.7553 Intermediate Similarity NPC214387
0.7553 Intermediate Similarity NPC472973
0.7553 Intermediate Similarity NPC210216
0.7553 Intermediate Similarity NPC310236

  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 NPC229612 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
0.7579 Intermediate Similarity NPD7515 Phase 2
0.7558 Intermediate Similarity NPD8264 Approved
0.7333 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD5779 Approved
0.732 Intermediate Similarity NPD5778 Approved
0.7312 Intermediate Similarity NPD1696 Phase 3
0.73 Intermediate Similarity NPD4225 Approved
0.7273 Intermediate Similarity NPD5221 Approved
0.7273 Intermediate Similarity NPD5222 Approved
0.7273 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD5211 Phase 2
0.7245 Intermediate Similarity NPD7748 Approved
0.7238 Intermediate Similarity NPD6881 Approved
0.7238 Intermediate Similarity NPD6899 Approved
0.7228 Intermediate Similarity NPD7640 Approved
0.7228 Intermediate Similarity NPD6648 Approved
0.7228 Intermediate Similarity NPD7639 Approved
0.7216 Intermediate Similarity NPD6079 Approved
0.72 Intermediate Similarity NPD5173 Approved
0.7188 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD5344 Discontinued
0.7143 Intermediate Similarity NPD5697 Approved
0.7129 Intermediate Similarity NPD7638 Approved
0.7115 Intermediate Similarity NPD5141 Approved
0.7103 Intermediate Similarity NPD6883 Approved
0.7103 Intermediate Similarity NPD7290 Approved
0.7103 Intermediate Similarity NPD7102 Approved
0.7075 Intermediate Similarity NPD6011 Approved
0.7059 Intermediate Similarity NPD5286 Approved
0.7059 Intermediate Similarity NPD5285 Approved
0.7059 Intermediate Similarity NPD4696 Approved
0.7053 Intermediate Similarity NPD5279 Phase 3
0.7053 Intermediate Similarity NPD3618 Phase 1
0.7048 Intermediate Similarity NPD6675 Approved
0.7048 Intermediate Similarity NPD6402 Approved
0.7048 Intermediate Similarity NPD7128 Approved
0.7048 Intermediate Similarity NPD5739 Approved
0.7037 Intermediate Similarity NPD8130 Phase 1
0.7037 Intermediate Similarity NPD6869 Approved
0.7037 Intermediate Similarity NPD6847 Approved
0.7037 Intermediate Similarity NPD6650 Approved
0.7037 Intermediate Similarity NPD6649 Approved
0.7037 Intermediate Similarity NPD6617 Approved
0.703 Intermediate Similarity NPD7902 Approved
0.7027 Intermediate Similarity NPD7115 Discovery
0.701 Intermediate Similarity NPD6101 Approved
0.701 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD5328 Approved
0.7009 Intermediate Similarity NPD6014 Approved
0.7009 Intermediate Similarity NPD6012 Approved
0.7009 Intermediate Similarity NPD6013 Approved
0.699 Remote Similarity NPD5223 Approved
0.6972 Remote Similarity NPD8297 Approved
0.6972 Remote Similarity NPD6882 Approved
0.6957 Remote Similarity NPD4695 Discontinued
0.6947 Remote Similarity NPD5363 Approved
0.6931 Remote Similarity NPD4697 Phase 3
0.6923 Remote Similarity NPD5224 Approved
0.6923 Remote Similarity NPD5226 Approved
0.6923 Remote Similarity NPD5225 Approved
0.6923 Remote Similarity NPD4633 Approved
0.6916 Remote Similarity NPD7320 Approved
0.6869 Remote Similarity NPD6411 Approved
0.6869 Remote Similarity NPD7637 Suspended
0.6863 Remote Similarity NPD6083 Phase 2
0.6863 Remote Similarity NPD6084 Phase 2
0.6863 Remote Similarity NPD4755 Approved
0.6857 Remote Similarity NPD5175 Approved
0.6857 Remote Similarity NPD5174 Approved
0.6852 Remote Similarity NPD6373 Approved
0.6852 Remote Similarity NPD6372 Approved
0.6848 Remote Similarity NPD7645 Phase 2
0.6842 Remote Similarity NPD4786 Approved
0.6822 Remote Similarity NPD5701 Approved
0.6813 Remote Similarity NPD4756 Discovery
0.6809 Remote Similarity NPD3667 Approved
0.68 Remote Similarity NPD6399 Phase 3
0.6786 Remote Similarity NPD6868 Approved
0.6778 Remote Similarity NPD6942 Approved
0.6778 Remote Similarity NPD7339 Approved
0.6774 Remote Similarity NPD7525 Registered
0.6771 Remote Similarity NPD1694 Approved
0.6768 Remote Similarity NPD7838 Discovery
0.6757 Remote Similarity NPD4632 Approved
0.6739 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6735 Remote Similarity NPD5737 Approved
0.6735 Remote Similarity NPD6672 Approved
0.6733 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7900 Approved
0.6731 Remote Similarity NPD4700 Approved
0.6727 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6703 Remote Similarity NPD3701 Clinical (unspecified phase)
0.67 Remote Similarity NPD5281 Approved
0.67 Remote Similarity NPD5284 Approved
0.6667 Remote Similarity NPD4753 Phase 2
0.6667 Remote Similarity NPD6924 Approved
0.6667 Remote Similarity NPD5210 Approved
0.6667 Remote Similarity NPD3133 Approved
0.6667 Remote Similarity NPD4629 Approved
0.6667 Remote Similarity NPD6335 Approved
0.6667 Remote Similarity NPD5695 Phase 3
0.6667 Remote Similarity NPD3666 Approved
0.6667 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6926 Approved
0.6667 Remote Similarity NPD3665 Phase 1
0.6667 Remote Similarity NPD4195 Approved
0.6667 Remote Similarity NPD6929 Approved
0.6635 Remote Similarity NPD5290 Discontinued
0.6635 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6634 Remote Similarity NPD4202 Approved
0.6633 Remote Similarity NPD3573 Approved
0.6632 Remote Similarity NPD4270 Approved
0.6632 Remote Similarity NPD4269 Approved
0.6629 Remote Similarity NPD7152 Approved
0.6629 Remote Similarity NPD7151 Approved
0.6629 Remote Similarity NPD7150 Approved
0.6609 Remote Similarity NPD7101 Approved
0.6609 Remote Similarity NPD7100 Approved
0.6606 Remote Similarity NPD5168 Approved
0.6606 Remote Similarity NPD4730 Approved
0.6606 Remote Similarity NPD4729 Approved
0.6604 Remote Similarity NPD7632 Discontinued
0.66 Remote Similarity NPD5785 Approved
0.6596 Remote Similarity NPD4819 Approved
0.6596 Remote Similarity NPD6931 Approved
0.6596 Remote Similarity NPD4821 Approved
0.6596 Remote Similarity NPD6930 Phase 2
0.6596 Remote Similarity NPD7514 Phase 3
0.6596 Remote Similarity NPD7332 Phase 2
0.6596 Remote Similarity NPD4822 Approved
0.6596 Remote Similarity NPD4820 Approved
0.6579 Remote Similarity NPD6317 Approved
0.6579 Remote Similarity NPD6009 Approved
0.6562 Remote Similarity NPD5332 Approved
0.6562 Remote Similarity NPD5362 Discontinued
0.6562 Remote Similarity NPD6695 Phase 3
0.6562 Remote Similarity NPD5331 Approved
0.6559 Remote Similarity NPD4271 Approved
0.6559 Remote Similarity NPD4268 Approved
0.6559 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6559 Remote Similarity NPD7145 Approved
0.6548 Remote Similarity NPD4192 Approved
0.6548 Remote Similarity NPD4191 Approved
0.6548 Remote Similarity NPD368 Approved
0.6548 Remote Similarity NPD4193 Approved
0.6548 Remote Similarity NPD4194 Approved
0.6542 Remote Similarity NPD4754 Approved
0.6535 Remote Similarity NPD6050 Approved
0.6535 Remote Similarity NPD5694 Approved
0.6531 Remote Similarity NPD5690 Phase 2
0.6531 Remote Similarity NPD5280 Approved
0.6531 Remote Similarity NPD4519 Discontinued
0.6531 Remote Similarity NPD6684 Approved
0.6531 Remote Similarity NPD7334 Approved
0.6531 Remote Similarity NPD4623 Approved
0.6531 Remote Similarity NPD4694 Approved
0.6531 Remote Similarity NPD6409 Approved
0.6531 Remote Similarity NPD7146 Approved
0.6531 Remote Similarity NPD7521 Approved
0.6531 Remote Similarity NPD5330 Approved
0.6526 Remote Similarity NPD6902 Approved
0.6526 Remote Similarity NPD4790 Discontinued
0.6522 Remote Similarity NPD6933 Approved
0.6522 Remote Similarity NPD6314 Approved
0.6522 Remote Similarity NPD6313 Approved
0.6517 Remote Similarity NPD7143 Approved
0.6517 Remote Similarity NPD7144 Approved
0.6496 Remote Similarity NPD7503 Approved
0.6495 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6491 Remote Similarity NPD6274 Approved
0.6486 Remote Similarity NPD5169 Approved
0.6486 Remote Similarity NPD5250 Approved
0.6486 Remote Similarity NPD5248 Approved
0.6486 Remote Similarity NPD5135 Approved
0.6486 Remote Similarity NPD5251 Approved
0.6486 Remote Similarity NPD5249 Phase 3
0.6486 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4634 Approved
0.6486 Remote Similarity NPD5247 Approved
0.6476 Remote Similarity NPD5696 Approved
0.6465 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6458 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6455 Remote Similarity NPD5128 Approved
0.6452 Remote Similarity NPD6925 Approved
0.6452 Remote Similarity NPD5776 Phase 2
0.6436 Remote Similarity NPD5692 Phase 3
0.6429 Remote Similarity NPD5329 Approved
0.6429 Remote Similarity NPD5215 Approved
0.6429 Remote Similarity NPD5127 Approved
0.6429 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5216 Approved
0.6429 Remote Similarity NPD5217 Approved
0.6422 Remote Similarity NPD4767 Approved
0.6422 Remote Similarity NPD4768 Approved
0.6421 Remote Similarity NPD7509 Discontinued
0.6421 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6421 Remote Similarity NPD4252 Approved
0.6415 Remote Similarity NPD6404 Discontinued
0.641 Remote Similarity NPD6319 Approved
0.6404 Remote Similarity NPD6923 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