Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  353.188
LogP:  3.883
LogD:  2.985
LogS:  -3.873
# Rotatable Bonds:  4
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.759
Synthetic Accessibility Score:  4.092
Fsp3:  0.7
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:  -5.182
MDCK Permeability:  1.5135191461013164e-05
Pgp-inhibitor:  0.029
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.894
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.135
Plasma Protein Binding (PPB):  84.81822967529297%
Volume Distribution (VD):  0.37
Pgp-substrate:  11.726541519165039%

ADMET: Metabolism

CYP1A2-inhibitor:  0.022
CYP1A2-substrate:  0.195
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.695
CYP2C9-inhibitor:  0.067
CYP2C9-substrate:  0.972
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.399
CYP3A4-inhibitor:  0.029
CYP3A4-substrate:  0.095

ADMET: Excretion

Clearance (CL):  6.159
Half-life (T1/2):  0.869

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.213
Drug-inuced Liver Injury (DILI):  0.436
AMES Toxicity:  0.018
Rat Oral Acute Toxicity:  0.489
Maximum Recommended Daily Dose:  0.945
Skin Sensitization:  0.485
Carcinogencity:  0.734
Eye Corrosion:  0.652
Eye Irritation:  0.894
Respiratory Toxicity:  0.965

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General Info & Identifiers & Properties  
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Similar NPs/Drugs  

  Natural Product: NPC133253

Natural Product ID:  NPC133253
Common Name*:   3-Oxoanticopalic Acid
IUPAC Name:   (E)-5-[(1S,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
Synonyms:   3-Oxoanticopalic Acid
Standard InCHIKey:  HZIPQMQRBXJVNO-KSVKHWKZSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-13(12-18(22)23)6-8-15-14(2)7-9-16-19(3,4)17(21)10-11-20(15,16)5/h12,15-16H,2,6-11H2,1,3-5H3,(H,22,23)/b13-12+/t15-,16-,20+/m0/s1
SMILES:  C/C(=CC(=O)O)/CC[C@H]1C(=C)CC[C@H]2C(C)(C)C(=O)CC[C@]12C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2036467
PubChem CID:   13858184
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jep.2005.01.054]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. root n.a. DOI[10.1016/S0031-9422(01)00459-9]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[11575963]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. stem n.a. PMID[12770595]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[1294697]
NPO27878 Viola hondoensis Species Violaceae Eukaryota n.a. whole plant n.a. PMID[15356999]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[17156960]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1800637]
NPO32532 callicarpa longissima Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[22429052]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota roots n.a. n.a. PMID[24940955]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[2607355]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[26110519]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[26422318]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[2809609]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Seeds n.a. n.a. PMID[28134521]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota Fruits n.a. n.a. PMID[28218000]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31181920]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31418264]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8158155]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8277307]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Stem Bark n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14888 Pelargonium x hortorum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28433 Russula queletii Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28006 Pinus pumila Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27334 Siphula roccellaeformis Species Icmadophilaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27861 Laggera aurita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9367 Jacobaea argunensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16927 Erodendrum neriifolium n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28174 Poterium sanguisorba Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28345 Cladanthus arabicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28208 Salvia dichroa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28568 Hippeastrum aulicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27480 Pinna muricata Species Pinnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28191 Hardwickia pinnata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21387 Forsythia suspensa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28433 Russula queletii Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14888 Pelargonium x hortorum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28499 Aethalium septicum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20121 Afraegle paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27894 Rubus pungens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4094 Aspergillus ruber Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28074 Dianella revoluta Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28534 Athrixia elata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28262 Marasmius graminum Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28555 Adina trichotoma Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28253 Ceratiomyxa fruticulosa Species Ceratiomyxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15295 Polyachyrus sphaerocephalus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27220 Centaurea cheiranthifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27878 Viola hondoensis Species Violaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28305 Daphnandra johnsonii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13153 Callicarpa macrophylla Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27681 Mikania grazielae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28512 Astragalus glycyphyllos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28061 Gyrothyra underwoodiana Species Gyrothyraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28330 Colchicum arenarium Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28049 Piper callosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27318 Sideritis lanata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28139 Umbilicaria pustulata Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23272 Cassinia subtropica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27532 Lamprolobium fruticosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28321 Cortinellus berkeleyanus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17152 Pittocaulon bombycophole Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4266 Botryotrichum murorum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16983 Persea obovatifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27350 Scytalidium uredinicola Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28168 Armina maculata Species n.a. 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
NPT306 Cell Line PC-3 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[476536]
NPT681 Cell Line PC-12 Rattus norvegicus EC50 = 6000.0 nM PMID[476537]
NPT2740 Cell Line Neutrophils IC50 > 10.0 ug.mL-1 PMID[476538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 9.31 ug.mL-1 PMID[476536]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10.0 ug.mL-1 PMID[476536]

☑ 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 NPC133253 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
0.9701 High Similarity NPC21944
0.9559 High Similarity NPC109576
0.9559 High Similarity NPC56747
0.9559 High Similarity NPC180015
0.9559 High Similarity NPC130016
0.9286 High Similarity NPC476346
0.8873 High Similarity NPC20025
0.8806 High Similarity NPC107258
0.8767 High Similarity NPC61952
0.875 High Similarity NPC469803
0.8684 High Similarity NPC469806
0.8684 High Similarity NPC472867
0.8684 High Similarity NPC469799
0.8684 High Similarity NPC472239
0.8684 High Similarity NPC469804
0.8684 High Similarity NPC469805
0.8667 High Similarity NPC469798
0.8667 High Similarity NPC469797
0.8649 High Similarity NPC198240
0.863 High Similarity NPC19907
0.8571 High Similarity NPC3856
0.8571 High Similarity NPC279639
0.8514 High Similarity NPC97377
0.8514 High Similarity NPC165711
0.8493 Intermediate Similarity NPC65650
0.8462 Intermediate Similarity NPC181743
0.8462 Intermediate Similarity NPC178025
0.8462 Intermediate Similarity NPC16287
0.8442 Intermediate Similarity NPC142253
0.8442 Intermediate Similarity NPC3511
0.8406 Intermediate Similarity NPC259156
0.8406 Intermediate Similarity NPC242945
0.8378 Intermediate Similarity NPC180886
0.8354 Intermediate Similarity NPC60350
0.8228 Intermediate Similarity NPC87552
0.8209 Intermediate Similarity NPC127582
0.8158 Intermediate Similarity NPC239098
0.8148 Intermediate Similarity NPC476409
0.8148 Intermediate Similarity NPC476293
0.8125 Intermediate Similarity NPC8571
0.8101 Intermediate Similarity NPC49019
0.8077 Intermediate Similarity NPC40228
0.8077 Intermediate Similarity NPC90055
0.8077 Intermediate Similarity NPC278459
0.8077 Intermediate Similarity NPC471898
0.8056 Intermediate Similarity NPC139397
0.8049 Intermediate Similarity NPC48107
0.8026 Intermediate Similarity NPC91665
0.8026 Intermediate Similarity NPC472300
0.8025 Intermediate Similarity NPC472869
0.8 Intermediate Similarity NPC476795
0.8 Intermediate Similarity NPC472864
0.8 Intermediate Similarity NPC248758
0.8 Intermediate Similarity NPC19849
0.7975 Intermediate Similarity NPC94200
0.7975 Intermediate Similarity NPC238991
0.7975 Intermediate Similarity NPC302661
0.7975 Intermediate Similarity NPC320514
0.7971 Intermediate Similarity NPC202118
0.7971 Intermediate Similarity NPC197238
0.7945 Intermediate Similarity NPC265782
0.7945 Intermediate Similarity NPC307176
0.7945 Intermediate Similarity NPC251929
0.7945 Intermediate Similarity NPC260040
0.7945 Intermediate Similarity NPC2634
0.7927 Intermediate Similarity NPC136948
0.7922 Intermediate Similarity NPC471409
0.7922 Intermediate Similarity NPC74410
0.7922 Intermediate Similarity NPC59436
0.7922 Intermediate Similarity NPC179028
0.7922 Intermediate Similarity NPC275494
0.7917 Intermediate Similarity NPC260474
0.7917 Intermediate Similarity NPC188292
0.7917 Intermediate Similarity NPC155198
0.7895 Intermediate Similarity NPC263582
0.7887 Intermediate Similarity NPC185587
0.7875 Intermediate Similarity NPC102197
0.7875 Intermediate Similarity NPC474790
0.7875 Intermediate Similarity NPC97913
0.7875 Intermediate Similarity NPC474976
0.7867 Intermediate Similarity NPC476046
0.7867 Intermediate Similarity NPC237591
0.7867 Intermediate Similarity NPC241854
0.7867 Intermediate Similarity NPC183503
0.7867 Intermediate Similarity NPC161923
0.7867 Intermediate Similarity NPC3753
0.7867 Intermediate Similarity NPC18819
0.7867 Intermediate Similarity NPC46610
0.7867 Intermediate Similarity NPC251970
0.7867 Intermediate Similarity NPC283908
0.7867 Intermediate Similarity NPC103958
0.7857 Intermediate Similarity NPC475124
0.7857 Intermediate Similarity NPC285371
0.7857 Intermediate Similarity NPC469662
0.7848 Intermediate Similarity NPC477372
0.7838 Intermediate Similarity NPC54123
0.7838 Intermediate Similarity NPC160817
0.7838 Intermediate Similarity NPC190035
0.7831 Intermediate Similarity NPC472870
0.7831 Intermediate Similarity NPC72397
0.7831 Intermediate Similarity NPC104560
0.7831 Intermediate Similarity NPC117122
0.7826 Intermediate Similarity NPC60565
0.7821 Intermediate Similarity NPC308038
0.7805 Intermediate Similarity NPC186975
0.7794 Intermediate Similarity NPC276764
0.7794 Intermediate Similarity NPC472304
0.7792 Intermediate Similarity NPC257666
0.7792 Intermediate Similarity NPC266193
0.7792 Intermediate Similarity NPC132542
0.7778 Intermediate Similarity NPC476412
0.7778 Intermediate Similarity NPC164577
0.7778 Intermediate Similarity NPC472865
0.7778 Intermediate Similarity NPC96095
0.7765 Intermediate Similarity NPC23217
0.7765 Intermediate Similarity NPC474018
0.7765 Intermediate Similarity NPC473986
0.7763 Intermediate Similarity NPC476844
0.7763 Intermediate Similarity NPC192540
0.7763 Intermediate Similarity NPC279666
0.775 Intermediate Similarity NPC268122
0.7746 Intermediate Similarity NPC251118
0.7738 Intermediate Similarity NPC36668
0.7738 Intermediate Similarity NPC118011
0.7738 Intermediate Similarity NPC262043
0.7733 Intermediate Similarity NPC474228
0.7733 Intermediate Similarity NPC303613
0.7733 Intermediate Similarity NPC472813
0.7733 Intermediate Similarity NPC35656
0.7733 Intermediate Similarity NPC247586
0.7722 Intermediate Similarity NPC26139
0.7714 Intermediate Similarity NPC288253
0.7711 Intermediate Similarity NPC236618
0.7703 Intermediate Similarity NPC235586
0.7703 Intermediate Similarity NPC35734
0.7703 Intermediate Similarity NPC159577
0.7703 Intermediate Similarity NPC282593
0.7692 Intermediate Similarity NPC62336
0.7692 Intermediate Similarity NPC475994
0.7683 Intermediate Similarity NPC474537
0.7683 Intermediate Similarity NPC255174
0.7683 Intermediate Similarity NPC29447
0.7683 Intermediate Similarity NPC106416
0.7683 Intermediate Similarity NPC269638
0.7683 Intermediate Similarity NPC476426
0.7683 Intermediate Similarity NPC65661
0.7683 Intermediate Similarity NPC86316
0.7674 Intermediate Similarity NPC476416
0.7671 Intermediate Similarity NPC87141
0.7671 Intermediate Similarity NPC310992
0.7662 Intermediate Similarity NPC7629
0.7662 Intermediate Similarity NPC151622
0.7662 Intermediate Similarity NPC472305
0.7662 Intermediate Similarity NPC69143
0.7662 Intermediate Similarity NPC1254
0.7654 Intermediate Similarity NPC215893
0.7654 Intermediate Similarity NPC118423
0.7654 Intermediate Similarity NPC105803
0.7654 Intermediate Similarity NPC41539
0.7647 Intermediate Similarity NPC60772
0.7647 Intermediate Similarity NPC51486
0.7647 Intermediate Similarity NPC476369
0.7647 Intermediate Similarity NPC472866
0.7647 Intermediate Similarity NPC476437
0.7647 Intermediate Similarity NPC27610
0.7647 Intermediate Similarity NPC56905
0.7639 Intermediate Similarity NPC81907
0.7639 Intermediate Similarity NPC255781
0.7632 Intermediate Similarity NPC309852
0.7632 Intermediate Similarity NPC75485
0.7632 Intermediate Similarity NPC213223
0.7632 Intermediate Similarity NPC474796
0.7632 Intermediate Similarity NPC329866
0.7632 Intermediate Similarity NPC474797
0.7632 Intermediate Similarity NPC168975
0.7625 Intermediate Similarity NPC274050
0.7625 Intermediate Similarity NPC229584
0.7625 Intermediate Similarity NPC14203
0.7625 Intermediate Similarity NPC162632
0.7625 Intermediate Similarity NPC263272
0.7625 Intermediate Similarity NPC267691
0.7625 Intermediate Similarity NPC147066
0.7606 Intermediate Similarity NPC150162
0.7606 Intermediate Similarity NPC212210
0.76 Intermediate Similarity NPC115023
0.7595 Intermediate Similarity NPC170394
0.7595 Intermediate Similarity NPC231431
0.7595 Intermediate Similarity NPC192329
0.7595 Intermediate Similarity NPC477371
0.759 Intermediate Similarity NPC322159
0.759 Intermediate Similarity NPC472986
0.759 Intermediate Similarity NPC472985
0.759 Intermediate Similarity NPC82979
0.7571 Intermediate Similarity NPC329416
0.7571 Intermediate Similarity NPC317177
0.7571 Intermediate Similarity NPC317025
0.7571 Intermediate Similarity NPC326645
0.7571 Intermediate Similarity NPC213152
0.7568 Intermediate Similarity NPC256846
0.7568 Intermediate Similarity NPC286814

  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 NPC133253 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
0.8056 Intermediate Similarity NPD4137 Phase 3
0.7945 Intermediate Similarity NPD4691 Approved
0.7945 Intermediate Similarity NPD4747 Approved
0.7632 Intermediate Similarity NPD4058 Approved
0.76 Intermediate Similarity NPD5276 Approved
0.759 Intermediate Similarity NPD4623 Approved
0.759 Intermediate Similarity NPD4519 Discontinued
0.7571 Intermediate Similarity NPD4193 Approved
0.7571 Intermediate Similarity NPD4194 Approved
0.7571 Intermediate Similarity NPD4192 Approved
0.7571 Intermediate Similarity NPD4191 Approved
0.7531 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4695 Discontinued
0.7432 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4687 Approved
0.7403 Intermediate Similarity NPD5733 Approved
0.7317 Intermediate Similarity NPD4223 Phase 3
0.7317 Intermediate Similarity NPD4221 Approved
0.7176 Intermediate Similarity NPD6409 Approved
0.7176 Intermediate Similarity NPD6684 Approved
0.7176 Intermediate Similarity NPD5330 Approved
0.7176 Intermediate Similarity NPD7521 Approved
0.7176 Intermediate Similarity NPD7334 Approved
0.7176 Intermediate Similarity NPD7146 Approved
0.7159 Intermediate Similarity NPD7515 Phase 2
0.7143 Intermediate Similarity NPD3665 Phase 1
0.7143 Intermediate Similarity NPD3666 Approved
0.7143 Intermediate Similarity NPD3133 Approved
0.7143 Intermediate Similarity NPD4197 Approved
0.7143 Intermediate Similarity NPD287 Approved
0.7126 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD3573 Approved
0.7059 Intermediate Similarity NPD5329 Approved
0.7037 Intermediate Similarity NPD3617 Approved
0.7037 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD5208 Approved
0.7011 Intermediate Similarity NPD5737 Approved
0.7011 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6903 Approved
0.7011 Intermediate Similarity NPD6672 Approved
0.7 Intermediate Similarity NPD7748 Approved
0.6977 Remote Similarity NPD4138 Approved
0.6977 Remote Similarity NPD4689 Approved
0.6977 Remote Similarity NPD5205 Approved
0.6977 Remote Similarity NPD4693 Phase 3
0.6977 Remote Similarity NPD4688 Approved
0.6977 Remote Similarity NPD3618 Phase 1
0.6977 Remote Similarity NPD4690 Approved
0.6966 Remote Similarity NPD5281 Approved
0.6966 Remote Similarity NPD5284 Approved
0.6966 Remote Similarity NPD5693 Phase 1
0.6932 Remote Similarity NPD6904 Approved
0.6932 Remote Similarity NPD6673 Approved
0.6932 Remote Similarity NPD6080 Approved
0.6905 Remote Similarity NPD3667 Approved
0.6786 Remote Similarity NPD8028 Phase 2
0.6782 Remote Similarity NPD6098 Approved
0.6782 Remote Similarity NPD4694 Approved
0.6782 Remote Similarity NPD5280 Approved
0.6782 Remote Similarity NPD5690 Phase 2
0.6782 Remote Similarity NPD5279 Phase 3
0.6782 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6083 Phase 2
0.6774 Remote Similarity NPD7902 Approved
0.6774 Remote Similarity NPD6084 Phase 2
0.6744 Remote Similarity NPD4786 Approved
0.6742 Remote Similarity NPD5328 Approved
0.6742 Remote Similarity NPD4753 Phase 2
0.6739 Remote Similarity NPD5695 Phase 3
0.6711 Remote Similarity NPD7331 Phase 2
0.6703 Remote Similarity NPD6399 Phase 3
0.6702 Remote Similarity NPD5696 Approved
0.6667 Remote Similarity NPD1694 Approved
0.6667 Remote Similarity NPD5692 Phase 3
0.6667 Remote Similarity NPD5207 Approved
0.6667 Remote Similarity NPD7614 Phase 1
0.6632 Remote Similarity NPD7640 Approved
0.6632 Remote Similarity NPD7639 Approved
0.6632 Remote Similarity NPD6404 Discontinued
0.663 Remote Similarity NPD7901 Clinical (unspecified phase)
0.663 Remote Similarity NPD6001 Approved
0.663 Remote Similarity NPD7900 Approved
0.6628 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6593 Remote Similarity NPD6079 Approved
0.6593 Remote Similarity NPD5694 Approved
0.6593 Remote Similarity NPD6050 Approved
0.6559 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6552 Remote Similarity NPD3668 Phase 3
0.6548 Remote Similarity NPD4195 Approved
0.6526 Remote Similarity NPD4225 Approved
0.6526 Remote Similarity NPD7638 Approved
0.6522 Remote Similarity NPD4202 Approved
0.6484 Remote Similarity NPD5785 Approved
0.6484 Remote Similarity NPD4096 Approved
0.6477 Remote Similarity NPD5363 Approved
0.6463 Remote Similarity NPD8039 Approved
0.6413 Remote Similarity NPD7637 Suspended
0.6383 Remote Similarity NPD4629 Approved
0.6383 Remote Similarity NPD5210 Approved
0.6364 Remote Similarity NPD7341 Phase 2
0.6337 Remote Similarity NPD6686 Approved
0.6327 Remote Similarity NPD5211 Phase 2
0.6322 Remote Similarity NPD4270 Approved
0.6322 Remote Similarity NPD4269 Approved
0.6316 Remote Similarity NPD5222 Approved
0.6316 Remote Similarity NPD7732 Phase 3
0.6316 Remote Similarity NPD4697 Phase 3
0.6316 Remote Similarity NPD5221 Approved
0.6316 Remote Similarity NPD5220 Clinical (unspecified phase)
0.631 Remote Similarity NPD4756 Discovery
0.63 Remote Similarity NPD6675 Approved
0.63 Remote Similarity NPD5739 Approved
0.63 Remote Similarity NPD6402 Approved
0.63 Remote Similarity NPD7128 Approved
0.6292 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6282 Remote Similarity NPD4224 Phase 2
0.6279 Remote Similarity NPD4252 Approved
0.6279 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6277 Remote Similarity NPD5769 Clinical (unspecified phase)
0.6264 Remote Similarity NPD4518 Approved
0.625 Remote Similarity NPD4755 Approved
0.625 Remote Similarity NPD5173 Approved
0.625 Remote Similarity NPD5362 Discontinued
0.625 Remote Similarity NPD4788 Approved
0.6238 Remote Similarity NPD5701 Approved
0.6238 Remote Similarity NPD5697 Approved
0.6234 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6211 Remote Similarity NPD5654 Approved
0.6211 Remote Similarity NPD6048 Clinical (unspecified phase)
0.6211 Remote Similarity NPD6049 Phase 2
0.6207 Remote Similarity NPD4139 Approved
0.6207 Remote Similarity NPD4692 Approved
0.62 Remote Similarity NPD5141 Approved
0.618 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6881 Approved
0.6176 Remote Similarity NPD7320 Approved
0.6176 Remote Similarity NPD6899 Approved
0.6176 Remote Similarity NPD6011 Approved
0.617 Remote Similarity NPD5133 Approved
0.617 Remote Similarity NPD5779 Approved
0.617 Remote Similarity NPD5778 Approved
0.6168 Remote Similarity NPD7115 Discovery
0.6164 Remote Similarity NPD4219 Approved
0.6136 Remote Similarity NPD5209 Approved
0.6122 Remote Similarity NPD5285 Approved
0.6122 Remote Similarity NPD4696 Approved
0.6122 Remote Similarity NPD5286 Approved
0.6122 Remote Similarity NPD4700 Approved
0.6117 Remote Similarity NPD6372 Approved
0.6117 Remote Similarity NPD6014 Approved
0.6117 Remote Similarity NPD6013 Approved
0.6117 Remote Similarity NPD6373 Approved
0.6117 Remote Similarity NPD6012 Approved
0.6111 Remote Similarity NPD1696 Phase 3
0.6111 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6105 Remote Similarity NPD5122 Clinical (unspecified phase)
0.61 Remote Similarity NPD6052 Approved
0.6087 Remote Similarity NPD4220 Pre-registration
0.6082 Remote Similarity NPD5959 Approved
0.6071 Remote Similarity NPD8264 Approved
0.6067 Remote Similarity NPD3971 Phase 1
0.6067 Remote Similarity NPD7154 Phase 3
0.6064 Remote Similarity NPD6411 Approved
0.6061 Remote Similarity NPD5223 Approved
0.6058 Remote Similarity NPD7290 Approved
0.6058 Remote Similarity NPD6883 Approved
0.6058 Remote Similarity NPD7102 Approved
0.6047 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6044 Remote Similarity NPD5786 Approved
0.604 Remote Similarity NPD5909 Discontinued
0.6027 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6 Remote Similarity NPD5226 Approved
0.6 Remote Similarity NPD6869 Approved
0.6 Remote Similarity NPD5091 Approved
0.6 Remote Similarity NPD8130 Phase 1
0.6 Remote Similarity NPD6617 Approved
0.6 Remote Similarity NPD6650 Approved
0.6 Remote Similarity NPD4633 Approved
0.6 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6 Remote Similarity NPD5225 Approved
0.6 Remote Similarity NPD6649 Approved
0.6 Remote Similarity NPD7632 Discontinued
0.6 Remote Similarity NPD6847 Approved
0.6 Remote Similarity NPD5224 Approved
0.598 Remote Similarity NPD6008 Approved
0.5972 Remote Similarity NPD3172 Approved
0.596 Remote Similarity NPD2066 Phase 3
0.5957 Remote Similarity NPD46 Approved
0.5957 Remote Similarity NPD6698 Approved
0.5949 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5943 Remote Similarity NPD6882 Approved
0.5943 Remote Similarity NPD8297 Approved
0.5941 Remote Similarity NPD4754 Approved
0.5941 Remote Similarity NPD5175 Approved
0.5941 Remote Similarity NPD5174 Approved
0.593 Remote Similarity NPD5776 Phase 2
0.593 Remote Similarity NPD6925 Approved
0.5922 Remote Similarity NPD6614 Approved
0.5922 Remote Similarity NPD6412 Phase 2
0.5918 Remote Similarity NPD3495 Discontinued

  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