Structure

Physi-Chem Properties

Molecular Weight:  362.25
Volume:  396.57
LogP:  4.832
LogD:  3.463
LogS:  -4.255
# Rotatable Bonds:  6
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.543
Synthetic Accessibility Score:  4.149
Fsp3:  0.727
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.944
MDCK Permeability:  3.4547974792076275e-05
Pgp-inhibitor:  0.032
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.664
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.269
Plasma Protein Binding (PPB):  85.46316528320312%
Volume Distribution (VD):  0.332
Pgp-substrate:  20.42826271057129%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.047
CYP2C19-inhibitor:  0.011
CYP2C19-substrate:  0.295
CYP2C9-inhibitor:  0.057
CYP2C9-substrate:  0.939
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.297
CYP3A4-inhibitor:  0.052
CYP3A4-substrate:  0.178

ADMET: Excretion

Clearance (CL):  2.576
Half-life (T1/2):  0.5

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.275
Drug-inuced Liver Injury (DILI):  0.426
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.076
Maximum Recommended Daily Dose:  0.96
Skin Sensitization:  0.701
Carcinogencity:  0.237
Eye Corrosion:  0.928
Eye Irritation:  0.895
Respiratory Toxicity:  0.968

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  Natural Product: NPC170303

Natural Product ID:  NPC170303
Common Name*:   3Beta-Acetoxycopalic Acid
IUPAC Name:   (E)-5-[(1S,4aR,6S,8aR)-6-acetyloxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
Synonyms:  
Standard InCHIKey:  OMNJRQNCWHCCBZ-BULWIKRESA-N
Standard InCHI:  InChI=1S/C22H34O4/c1-14(13-20(24)25)7-9-17-15(2)8-10-18-21(4,5)19(26-16(3)23)11-12-22(17,18)6/h13,17-19H,2,7-12H2,1,3-6H3,(H,24,25)/b14-13+/t17-,18-,19-,22+/m0/s1
SMILES:  CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CCC(=C)[C@@H]2CC/C(=C/C(=O)O)/C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3315351
PubChem CID:   13858192
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]
NPO28378 Kokoona ochracea Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1800637]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota roots n.a. n.a. PMID[24940955]
NPO13331 Solidago canadensis Species Asteraceae Eukaryota n.a. Canada n.a. PMID[24999828]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. PMID[2607355]
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]
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 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]
NPO9138 Syzygium cumini Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO27689 Mentha pulegium Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28378 Kokoona ochracea Species Celastraceae 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]
NPO28433 Russula queletii Species Russulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14888 Pelargonium x hortorum Species Geraniaceae 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]
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]
NPO28276 Artemisia argyi Species Asteraceae 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[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]
NPO17152 Pittocaulon bombycophole Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20121 Afraegle paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28253 Ceratiomyxa fruticulosa Species Ceratiomyxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28305 Daphnandra johnsonii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28276 Artemisia argyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28074 Dianella revoluta Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27878 Viola hondoensis Species Violaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28061 Gyrothyra underwoodiana Species Gyrothyraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28512 Astragalus glycyphyllos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27318 Sideritis lanata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27220 Centaurea cheiranthifolia 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]
NPO27681 Mikania grazielae 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]
NPO20443 Cratoxylum pruniflorum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28568 Hippeastrum aulicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28330 Colchicum arenarium Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28124 Tamarix gallica Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23272 Cassinia subtropica 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]
NPO16983 Persea obovatifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27689 Mentha pulegium Species Lamiaceae 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]
NPO28433 Russula queletii Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27894 Rubus pungens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4266 Botryotrichum murorum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27350 Scytalidium uredinicola Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15295 Polyachyrus sphaerocephalus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28168 Armina maculata Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28534 Athrixia elata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27604 Erythrina burttii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]
NPO27847 Suillus granulatus Species Suillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28139 Umbilicaria pustulata Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9367 Jacobaea argunensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27861 Laggera aurita Species Asteraceae 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]
NPO28174 Poterium sanguisorba Species Rosaceae 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]
NPO27480 Pinna muricata Species Pinnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13331 Solidago canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14888 Pelargonium x hortorum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28049 Piper callosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4094 Aspergillus ruber Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28555 Adina trichotoma Species Rubiaceae 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]
NPO28262 Marasmius graminum Species Marasmiaceae 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
NPT3971 Individual Protein Taste receptor type 2 member 31 Homo sapiens IC50 = 8000.0 nM PMID[529654]

☑ 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 NPC170303 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
0.961 High Similarity NPC256112
0.9487 High Similarity NPC476927
0.9367 High Similarity NPC306951
0.9351 High Similarity NPC281880
0.9231 High Similarity NPC159148
0.9114 High Similarity NPC2524
0.9 High Similarity NPC79945
0.8929 High Similarity NPC78973
0.8902 High Similarity NPC175145
0.8902 High Similarity NPC131813
0.8902 High Similarity NPC475069
0.8889 High Similarity NPC102048
0.8824 High Similarity NPC329842
0.881 High Similarity NPC170633
0.8795 High Similarity NPC166857
0.878 High Similarity NPC474013
0.8721 High Similarity NPC53555
0.8721 High Similarity NPC38232
0.8718 High Similarity NPC132542
0.869 High Similarity NPC291665
0.869 High Similarity NPC104560
0.8659 High Similarity NPC96055
0.8625 High Similarity NPC469802
0.8605 High Similarity NPC472811
0.8554 High Similarity NPC109528
0.8554 High Similarity NPC35933
0.8537 High Similarity NPC311070
0.8519 High Similarity NPC142163
0.8506 High Similarity NPC472812
0.8506 High Similarity NPC7349
0.85 High Similarity NPC242767
0.8471 Intermediate Similarity NPC93411
0.8415 Intermediate Similarity NPC471218
0.8409 Intermediate Similarity NPC105490
0.8409 Intermediate Similarity NPC57117
0.8391 Intermediate Similarity NPC72845
0.8372 Intermediate Similarity NPC314727
0.8372 Intermediate Similarity NPC474396
0.8372 Intermediate Similarity NPC246028
0.8372 Intermediate Similarity NPC262858
0.8372 Intermediate Similarity NPC16265
0.8372 Intermediate Similarity NPC82876
0.8372 Intermediate Similarity NPC50488
0.8372 Intermediate Similarity NPC472240
0.8315 Intermediate Similarity NPC276110
0.8315 Intermediate Similarity NPC472441
0.8295 Intermediate Similarity NPC139692
0.8295 Intermediate Similarity NPC162615
0.8295 Intermediate Similarity NPC152778
0.8295 Intermediate Similarity NPC205034
0.8295 Intermediate Similarity NPC476304
0.8293 Intermediate Similarity NPC25554
0.8276 Intermediate Similarity NPC310479
0.8276 Intermediate Similarity NPC232202
0.8276 Intermediate Similarity NPC182136
0.8276 Intermediate Similarity NPC221111
0.8276 Intermediate Similarity NPC280149
0.8272 Intermediate Similarity NPC100906
0.8256 Intermediate Similarity NPC472810
0.8256 Intermediate Similarity NPC472809
0.8256 Intermediate Similarity NPC106332
0.825 Intermediate Similarity NPC189206
0.825 Intermediate Similarity NPC283619
0.8242 Intermediate Similarity NPC478056
0.8242 Intermediate Similarity NPC325229
0.8242 Intermediate Similarity NPC275086
0.8235 Intermediate Similarity NPC474970
0.8235 Intermediate Similarity NPC329692
0.8222 Intermediate Similarity NPC134072
0.8222 Intermediate Similarity NPC234993
0.8222 Intermediate Similarity NPC473153
0.8222 Intermediate Similarity NPC16967
0.8222 Intermediate Similarity NPC242848
0.8214 Intermediate Similarity NPC302360
0.8202 Intermediate Similarity NPC470255
0.8202 Intermediate Similarity NPC279410
0.8202 Intermediate Similarity NPC119562
0.8202 Intermediate Similarity NPC476186
0.8193 Intermediate Similarity NPC286786
0.8182 Intermediate Similarity NPC74296
0.8182 Intermediate Similarity NPC110923
0.8182 Intermediate Similarity NPC177641
0.8171 Intermediate Similarity NPC269791
0.8161 Intermediate Similarity NPC146554
0.8152 Intermediate Similarity NPC251680
0.8152 Intermediate Similarity NPC266955
0.8152 Intermediate Similarity NPC38855
0.8152 Intermediate Similarity NPC324841
0.814 Intermediate Similarity NPC131329
0.814 Intermediate Similarity NPC245004
0.8132 Intermediate Similarity NPC73911
0.8132 Intermediate Similarity NPC141401
0.8132 Intermediate Similarity NPC51499
0.8132 Intermediate Similarity NPC253826
0.8118 Intermediate Similarity NPC30984
0.8118 Intermediate Similarity NPC476602
0.8118 Intermediate Similarity NPC164424
0.8118 Intermediate Similarity NPC191965
0.8101 Intermediate Similarity NPC201048
0.8101 Intermediate Similarity NPC306727
0.8101 Intermediate Similarity NPC476366
0.8095 Intermediate Similarity NPC57370
0.8095 Intermediate Similarity NPC132386
0.8095 Intermediate Similarity NPC52108
0.8095 Intermediate Similarity NPC474789
0.8095 Intermediate Similarity NPC42476
0.809 Intermediate Similarity NPC214697
0.8072 Intermediate Similarity NPC14203
0.8072 Intermediate Similarity NPC40228
0.8072 Intermediate Similarity NPC229584
0.8072 Intermediate Similarity NPC195334
0.8072 Intermediate Similarity NPC290495
0.8065 Intermediate Similarity NPC303559
0.8065 Intermediate Similarity NPC118174
0.8065 Intermediate Similarity NPC115899
0.8046 Intermediate Similarity NPC229612
0.8046 Intermediate Similarity NPC7280
0.8046 Intermediate Similarity NPC473879
0.8043 Intermediate Similarity NPC278673
0.8043 Intermediate Similarity NPC159763
0.8043 Intermediate Similarity NPC278386
0.8043 Intermediate Similarity NPC218107
0.8043 Intermediate Similarity NPC124512
0.8043 Intermediate Similarity NPC473154
0.8025 Intermediate Similarity NPC470711
0.8025 Intermediate Similarity NPC470428
0.8025 Intermediate Similarity NPC470758
0.8025 Intermediate Similarity NPC61952
0.8023 Intermediate Similarity NPC137306
0.8023 Intermediate Similarity NPC325594
0.8023 Intermediate Similarity NPC84121
0.8023 Intermediate Similarity NPC473226
0.8023 Intermediate Similarity NPC73038
0.8023 Intermediate Similarity NPC322159
0.8022 Intermediate Similarity NPC276103
0.8022 Intermediate Similarity NPC250757
0.8022 Intermediate Similarity NPC301534
0.8022 Intermediate Similarity NPC195366
0.8022 Intermediate Similarity NPC190713
0.8022 Intermediate Similarity NPC114743
0.8022 Intermediate Similarity NPC54248
0.8 Intermediate Similarity NPC191521
0.8 Intermediate Similarity NPC474922
0.8 Intermediate Similarity NPC469697
0.8 Intermediate Similarity NPC140277
0.8 Intermediate Similarity NPC74751
0.8 Intermediate Similarity NPC107258
0.8 Intermediate Similarity NPC32223
0.7979 Intermediate Similarity NPC475038
0.7979 Intermediate Similarity NPC109195
0.7979 Intermediate Similarity NPC320447
0.7978 Intermediate Similarity NPC473675
0.7978 Intermediate Similarity NPC212948
0.7976 Intermediate Similarity NPC155521
0.7957 Intermediate Similarity NPC16601
0.7957 Intermediate Similarity NPC474190
0.7957 Intermediate Similarity NPC471413
0.7957 Intermediate Similarity NPC471041
0.7955 Intermediate Similarity NPC470734
0.7955 Intermediate Similarity NPC50070
0.7955 Intermediate Similarity NPC20946
0.7952 Intermediate Similarity NPC10636
0.7935 Intermediate Similarity NPC474343
0.7935 Intermediate Similarity NPC99726
0.7931 Intermediate Similarity NPC264546
0.7931 Intermediate Similarity NPC473891
0.7927 Intermediate Similarity NPC198240
0.7927 Intermediate Similarity NPC476949
0.7927 Intermediate Similarity NPC239098
0.7927 Intermediate Similarity NPC184737
0.7927 Intermediate Similarity NPC476314
0.7912 Intermediate Similarity NPC134067
0.7907 Intermediate Similarity NPC52628
0.7907 Intermediate Similarity NPC65661
0.7901 Intermediate Similarity NPC470749
0.7895 Intermediate Similarity NPC478057
0.7895 Intermediate Similarity NPC72151
0.7895 Intermediate Similarity NPC95899
0.7895 Intermediate Similarity NPC473283
0.7895 Intermediate Similarity NPC329345
0.7895 Intermediate Similarity NPC475526
0.7889 Intermediate Similarity NPC214756
0.7889 Intermediate Similarity NPC472641
0.7889 Intermediate Similarity NPC272075
0.7889 Intermediate Similarity NPC472640
0.7889 Intermediate Similarity NPC472303
0.7889 Intermediate Similarity NPC476416
0.7889 Intermediate Similarity NPC472871
0.7889 Intermediate Similarity NPC295643
0.7882 Intermediate Similarity NPC139206
0.7882 Intermediate Similarity NPC49208
0.7882 Intermediate Similarity NPC12283
0.7882 Intermediate Similarity NPC477124
0.7882 Intermediate Similarity NPC474193
0.7882 Intermediate Similarity NPC23748
0.7875 Intermediate Similarity NPC71152
0.7872 Intermediate Similarity NPC247701
0.7872 Intermediate Similarity NPC295110
0.7872 Intermediate Similarity NPC115862
0.7872 Intermediate Similarity NPC473160

  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 NPC170303 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
0.8152 Intermediate Similarity NPD7639 Approved
0.8152 Intermediate Similarity NPD7640 Approved
0.8043 Intermediate Similarity NPD7638 Approved
0.8043 Intermediate Similarity NPD4225 Approved
0.8 Intermediate Similarity NPD7748 Approved
0.7778 Intermediate Similarity NPD7515 Phase 2
0.7765 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD7902 Approved
0.7609 Intermediate Similarity NPD7900 Approved
0.7609 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7632 Discontinued
0.7416 Intermediate Similarity NPD7146 Approved
0.7416 Intermediate Similarity NPD7334 Approved
0.7416 Intermediate Similarity NPD7521 Approved
0.7416 Intermediate Similarity NPD6684 Approved
0.7416 Intermediate Similarity NPD5330 Approved
0.7416 Intermediate Similarity NPD6409 Approved
0.7412 Intermediate Similarity NPD7645 Phase 2
0.7363 Intermediate Similarity NPD6051 Approved
0.7326 Intermediate Similarity NPD7525 Registered
0.7312 Intermediate Similarity NPD6399 Phase 3
0.7253 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD6672 Approved
0.7253 Intermediate Similarity NPD6903 Approved
0.7253 Intermediate Similarity NPD5737 Approved
0.7222 Intermediate Similarity NPD3618 Phase 1
0.7216 Intermediate Similarity NPD6648 Approved
0.7204 Intermediate Similarity NPD7637 Suspended
0.72 Intermediate Similarity NPD5739 Approved
0.72 Intermediate Similarity NPD7128 Approved
0.72 Intermediate Similarity NPD6675 Approved
0.72 Intermediate Similarity NPD6402 Approved
0.7191 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD5328 Approved
0.7143 Intermediate Similarity NPD3573 Approved
0.7143 Intermediate Similarity NPD8264 Approved
0.7143 Intermediate Similarity NPD5344 Discontinued
0.7111 Intermediate Similarity NPD1694 Approved
0.7079 Intermediate Similarity NPD6695 Phase 3
0.7059 Intermediate Similarity NPD6899 Approved
0.7059 Intermediate Similarity NPD6881 Approved
0.7059 Intermediate Similarity NPD7320 Approved
0.7021 Intermediate Similarity NPD6079 Approved
0.7021 Intermediate Similarity NPD8035 Phase 2
0.7021 Intermediate Similarity NPD8034 Phase 2
0.701 Intermediate Similarity NPD6084 Phase 2
0.701 Intermediate Similarity NPD6083 Phase 2
0.7009 Intermediate Similarity NPD7115 Discovery
0.7 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.699 Remote Similarity NPD6372 Approved
0.699 Remote Similarity NPD6373 Approved
0.6979 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6961 Remote Similarity NPD5701 Approved
0.6961 Remote Similarity NPD5697 Approved
0.6947 Remote Similarity NPD5778 Approved
0.6947 Remote Similarity NPD5779 Approved
0.6941 Remote Similarity NPD6942 Approved
0.6941 Remote Similarity NPD7339 Approved
0.6923 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7102 Approved
0.6923 Remote Similarity NPD6883 Approved
0.6923 Remote Similarity NPD7290 Approved
0.6893 Remote Similarity NPD6686 Approved
0.6893 Remote Similarity NPD6011 Approved
0.6875 Remote Similarity NPD2685 Clinical (unspecified phase)
0.686 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6857 Remote Similarity NPD8130 Phase 1
0.6857 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6857 Remote Similarity NPD6650 Approved
0.6857 Remote Similarity NPD6617 Approved
0.6857 Remote Similarity NPD6869 Approved
0.6857 Remote Similarity NPD6649 Approved
0.6857 Remote Similarity NPD6847 Approved
0.6842 Remote Similarity NPD6411 Approved
0.6827 Remote Similarity NPD6014 Approved
0.6827 Remote Similarity NPD6013 Approved
0.6827 Remote Similarity NPD6012 Approved
0.6824 Remote Similarity NPD6924 Approved
0.6824 Remote Similarity NPD6926 Approved
0.6818 Remote Similarity NPD6929 Approved
0.6813 Remote Similarity NPD3665 Phase 1
0.6813 Remote Similarity NPD3666 Approved
0.6813 Remote Similarity NPD4786 Approved
0.6813 Remote Similarity NPD3133 Approved
0.6809 Remote Similarity NPD6904 Approved
0.6809 Remote Similarity NPD6080 Approved
0.6809 Remote Similarity NPD6673 Approved
0.6804 Remote Similarity NPD5695 Phase 3
0.6792 Remote Similarity NPD6882 Approved
0.6792 Remote Similarity NPD8297 Approved
0.6789 Remote Similarity NPD7328 Approved
0.6789 Remote Similarity NPD7327 Approved
0.6778 Remote Similarity NPD3667 Approved
0.6774 Remote Similarity NPD7750 Discontinued
0.6774 Remote Similarity NPD7524 Approved
0.6771 Remote Similarity NPD4202 Approved
0.6768 Remote Similarity NPD5696 Approved
0.6742 Remote Similarity NPD6930 Phase 2
0.6742 Remote Similarity NPD6931 Approved
0.6742 Remote Similarity NPD4695 Discontinued
0.6735 Remote Similarity NPD4697 Phase 3
0.6735 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6735 Remote Similarity NPD5222 Approved
0.6735 Remote Similarity NPD5221 Approved
0.6733 Remote Similarity NPD5211 Phase 2
0.6727 Remote Similarity NPD7516 Approved
0.6709 Remote Similarity NPD4191 Approved
0.6709 Remote Similarity NPD4193 Approved
0.6709 Remote Similarity NPD4194 Approved
0.6709 Remote Similarity NPD4192 Approved
0.6705 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6705 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6699 Remote Similarity NPD6008 Approved
0.6667 Remote Similarity NPD5173 Approved
0.6667 Remote Similarity NPD4755 Approved
0.6667 Remote Similarity NPD4623 Approved
0.6667 Remote Similarity NPD6933 Approved
0.6667 Remote Similarity NPD8377 Approved
0.6667 Remote Similarity NPD4519 Discontinued
0.6667 Remote Similarity NPD5693 Phase 1
0.6667 Remote Similarity NPD8294 Approved
0.6667 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6632 Remote Similarity NPD6101 Approved
0.6632 Remote Similarity NPD7285 Clinical (unspecified phase)
0.663 Remote Similarity NPD3668 Phase 3
0.6629 Remote Similarity NPD4195 Approved
0.6607 Remote Similarity NPD8296 Approved
0.6607 Remote Similarity NPD8033 Approved
0.6607 Remote Similarity NPD8378 Approved
0.6607 Remote Similarity NPD8380 Approved
0.6607 Remote Similarity NPD8335 Approved
0.6607 Remote Similarity NPD8379 Approved
0.6606 Remote Similarity NPD6868 Approved
0.6604 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6602 Remote Similarity NPD5141 Approved
0.6596 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6925 Approved
0.6591 Remote Similarity NPD5776 Phase 2
0.6588 Remote Similarity NPD7151 Approved
0.6588 Remote Similarity NPD7150 Approved
0.6588 Remote Similarity NPD7152 Approved
0.6562 Remote Similarity NPD5785 Approved
0.6556 Remote Similarity NPD7332 Phase 2
0.6556 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7509 Discontinued
0.6556 Remote Similarity NPD7514 Phase 3
0.6552 Remote Similarity NPD8039 Approved
0.6548 Remote Similarity NPD6923 Approved
0.6548 Remote Similarity NPD6922 Approved
0.6543 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6535 Remote Similarity NPD5286 Approved
0.6535 Remote Similarity NPD5285 Approved
0.6535 Remote Similarity NPD4696 Approved
0.6535 Remote Similarity NPD4700 Approved
0.6531 Remote Similarity NPD6001 Approved
0.6526 Remote Similarity NPD5208 Approved
0.6522 Remote Similarity NPD5362 Discontinued
0.6522 Remote Similarity NPD7154 Phase 3
0.6517 Remote Similarity NPD7145 Approved
0.6495 Remote Similarity NPD7087 Discontinued
0.6495 Remote Similarity NPD6050 Approved
0.6489 Remote Similarity NPD6098 Approved
0.6489 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6489 Remote Similarity NPD5279 Phase 3
0.6486 Remote Similarity NPD6335 Approved
0.6484 Remote Similarity NPD6902 Approved
0.6476 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5223 Approved
0.6471 Remote Similarity NPD7144 Approved
0.6471 Remote Similarity NPD7143 Approved
0.646 Remote Similarity NPD7503 Approved
0.6458 Remote Similarity NPD4753 Phase 2
0.6455 Remote Similarity NPD6274 Approved
0.6436 Remote Similarity NPD5290 Discontinued
0.6429 Remote Similarity NPD7101 Approved
0.6429 Remote Similarity NPD7100 Approved
0.6422 Remote Similarity NPD4632 Approved
0.6413 Remote Similarity NPD5209 Approved
0.6413 Remote Similarity NPD4223 Phase 3
0.6413 Remote Similarity NPD4221 Approved
0.6408 Remote Similarity NPD5224 Approved
0.6408 Remote Similarity NPD5225 Approved
0.6408 Remote Similarity NPD4633 Approved
0.6408 Remote Similarity NPD5226 Approved
0.6396 Remote Similarity NPD6317 Approved
0.6395 Remote Similarity NPD4243 Approved
0.6392 Remote Similarity NPD7838 Discovery
0.6392 Remote Similarity NPD46 Approved
0.6392 Remote Similarity NPD5692 Phase 3
0.6392 Remote Similarity NPD6698 Approved
0.6383 Remote Similarity NPD6893 Approved
0.6383 Remote Similarity NPD5329 Approved
0.6383 Remote Similarity NPD5363 Approved
0.6383 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6379 Remote Similarity NPD7507 Approved
0.6374 Remote Similarity NPD4819 Approved
0.6374 Remote Similarity NPD4822 Approved
0.6374 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6374 Remote Similarity NPD4820 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