Structure

Physi-Chem Properties

Molecular Weight:  378.24
Volume:  393.521
LogP:  4.285
LogD:  3.778
LogS:  -4.917
# Rotatable Bonds:  2
TPSA:  61.83
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.645
Synthetic Accessibility Score:  5.411
Fsp3:  0.909
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:  -5.059
MDCK Permeability:  2.4409690013271756e-05
Pgp-inhibitor:  0.989
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.175
30% Bioavailability (F30%):  0.488

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  84.93824005126953%
Volume Distribution (VD):  0.974
Pgp-substrate:  16.361482620239258%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.397
CYP2C19-inhibitor:  0.191
CYP2C19-substrate:  0.845
CYP2C9-inhibitor:  0.341
CYP2C9-substrate:  0.05
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.08
CYP3A4-inhibitor:  0.85
CYP3A4-substrate:  0.571

ADMET: Excretion

Clearance (CL):  8.05
Half-life (T1/2):  0.26

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.581
Drug-inuced Liver Injury (DILI):  0.581
AMES Toxicity:  0.101
Rat Oral Acute Toxicity:  0.126
Maximum Recommended Daily Dose:  0.65
Skin Sensitization:  0.364
Carcinogencity:  0.4
Eye Corrosion:  0.013
Eye Irritation:  0.042
Respiratory Toxicity:  0.754

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  Natural Product: NPC65133

Natural Product ID:  NPC65133
Common Name*:   Previtexilactone
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  VMSPIYCFMMEMSY-HREPXLEDSA-N
Standard InCHI:  InChI=1S/C22H34O5/c1-14-11-16(26-15(2)23)18-19(3,4)7-6-8-20(18,5)22(14)10-9-21(27-22)12-17(24)25-13-21/h14,16,18H,6-13H2,1-5H3/t14-,16-,18+,20+,21+,22-/m1/s1
SMILES:  CC(=O)O[C@@H]1C[C@@H](C)[C@@]2([C@@]3([C@@H]1C(C)(C)CCC3)C)CC[C@@]1(O2)COC(=O)C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2391699
PubChem CID:   21636179
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. fruit n.a. PMID[15577254]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[15621610]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. PMID[16180830]
NPO22123 Disepalum plagioneurum Species Annonaceae Eukaryota leaves Tam Kim, Cao Bang Province, in North Vietnam 2000-JUN PMID[16989521]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota whole plant Cholistan desert near district Bahawalpur (Punjab), Pakistan 2003-Oct PMID[20542692]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[2082684]
NPO18212 Rhododendron ferrugineum Species Ericaceae Eukaryota n.a. leaf n.a. PMID[21443171]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[21922656]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota fruits n.a. n.a. PMID[23327905]
NPO18530 Shigella flexneri Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26918643]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[28453270]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[3254039]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. aerial part n.a. PMID[3256207]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. PMID[3668556]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21875 Persea indica Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21373 Vitex trifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23135 Formica fusca Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18571 Drypetes roxburghii Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20678 Grindelia nana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21298 Leucanthemum maximum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19074 Buddleja variabilis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20184 Streptomyces misawanensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20808 Halopitys incurvus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16146 Osmundaria colensoi Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21636 Didemnum inarmatum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20536 Salvia nubicola Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21798 Dacrydium biforme Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21505 Calea megacephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17108 Lecanora lividocinerea Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7865 Scapania nemorea Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21875 Persea indica Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22062 Leptothorax acervorum Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22762 Eremophila serrulata Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21736 Abies nobilis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22582 Smenospongia echina Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22123 Disepalum plagioneurum Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14394 Hakea saligna Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22994 Cordyline indivisa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5952 Phegopteris bukoensis Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22323 Pinus picea Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22710 Acrocomia sclerocarpa Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12225 Amsinckia menziesii Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22248 Alkanna hirsutissima Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23218 Viscum coloratum Species Viscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23057 Primula hirsuta Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19921 Polyphaga sinensis Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21113 Coronophora gregaria Species Nitschkiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14247 Melaleuca uncinata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17785 Avrainvillea nigricans Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19694 Senecio scandens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22188 Piper aequale Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18212 Rhododendron ferrugineum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7080 Monascus purpureus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22819 Rodgersia podophylla Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21998 Corydalis cornuta Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23178 Jasminum grandiflorum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20360 Mentha pulegiformis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20043 Vallaris solanacea Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22940 Delphinium campylocentrum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22454 Picris radicata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18530 Shigella flexneri Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21247 Nephroma australe Species Nephromataceae 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
NPT994 Cell Line ZR-75-30 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[489619]
NPT116 Cell Line HL-60 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[489619]
NPT393 Cell Line HCT-116 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[489619]
NPT81 Cell Line A549 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[489619]

☑ 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 NPC65133 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
0.9512 High Similarity NPC471221
0.9277 High Similarity NPC221993
0.9 High Similarity NPC134227
0.8736 High Similarity NPC216137
0.8718 High Similarity NPC55508
0.859 High Similarity NPC109510
0.8588 High Similarity NPC477441
0.8537 High Similarity NPC125366
0.8434 Intermediate Similarity NPC71541
0.8415 Intermediate Similarity NPC474754
0.8409 Intermediate Similarity NPC470114
0.8391 Intermediate Similarity NPC476435
0.8354 Intermediate Similarity NPC474755
0.8353 Intermediate Similarity NPC477434
0.8352 Intermediate Similarity NPC116683
0.8333 Intermediate Similarity NPC13494
0.8313 Intermediate Similarity NPC471217
0.8313 Intermediate Similarity NPC471216
0.8295 Intermediate Similarity NPC477440
0.8295 Intermediate Similarity NPC477443
0.8261 Intermediate Similarity NPC266417
0.8235 Intermediate Similarity NPC476721
0.8222 Intermediate Similarity NPC474379
0.8202 Intermediate Similarity NPC477444
0.8202 Intermediate Similarity NPC477433
0.8202 Intermediate Similarity NPC477442
0.8171 Intermediate Similarity NPC307865
0.8171 Intermediate Similarity NPC143250
0.8161 Intermediate Similarity NPC476717
0.8161 Intermediate Similarity NPC474008
0.814 Intermediate Similarity NPC473299
0.8046 Intermediate Similarity NPC477445
0.8046 Intermediate Similarity NPC478111
0.8 Intermediate Similarity NPC470154
0.8 Intermediate Similarity NPC475743
0.7978 Intermediate Similarity NPC476379
0.7976 Intermediate Similarity NPC477287
0.7957 Intermediate Similarity NPC475785
0.7957 Intermediate Similarity NPC475765
0.7952 Intermediate Similarity NPC471151
0.7935 Intermediate Similarity NPC477495
0.7931 Intermediate Similarity NPC18953
0.7912 Intermediate Similarity NPC475878
0.7907 Intermediate Similarity NPC477284
0.7907 Intermediate Similarity NPC477446
0.7907 Intermediate Similarity NPC470155
0.7907 Intermediate Similarity NPC477447
0.7901 Intermediate Similarity NPC123122
0.7889 Intermediate Similarity NPC67653
0.7889 Intermediate Similarity NPC471459
0.7882 Intermediate Similarity NPC472943
0.7882 Intermediate Similarity NPC472951
0.7865 Intermediate Similarity NPC62202
0.7865 Intermediate Similarity NPC213658
0.7865 Intermediate Similarity NPC110365
0.7865 Intermediate Similarity NPC45833
0.7821 Intermediate Similarity NPC84562
0.7816 Intermediate Similarity NPC15091
0.7791 Intermediate Similarity NPC470156
0.7789 Intermediate Similarity NPC472144
0.7789 Intermediate Similarity NPC253995
0.7778 Intermediate Similarity NPC201607
0.7778 Intermediate Similarity NPC56777
0.7766 Intermediate Similarity NPC235109
0.7765 Intermediate Similarity NPC73013
0.7755 Intermediate Similarity NPC473701
0.7755 Intermediate Similarity NPC473526
0.7753 Intermediate Similarity NPC103782
0.7753 Intermediate Similarity NPC114378
0.7742 Intermediate Similarity NPC470424
0.7732 Intermediate Similarity NPC244969
0.7732 Intermediate Similarity NPC213528
0.7727 Intermediate Similarity NPC181871
0.7727 Intermediate Similarity NPC473336
0.7727 Intermediate Similarity NPC471044
0.7727 Intermediate Similarity NPC9060
0.7708 Intermediate Similarity NPC477656
0.7701 Intermediate Similarity NPC311642
0.7701 Intermediate Similarity NPC164289
0.7701 Intermediate Similarity NPC242771
0.7701 Intermediate Similarity NPC102156
0.7701 Intermediate Similarity NPC148740
0.7701 Intermediate Similarity NPC100366
0.7692 Intermediate Similarity NPC253618
0.7692 Intermediate Similarity NPC200580
0.7692 Intermediate Similarity NPC471222
0.7692 Intermediate Similarity NPC77001
0.7692 Intermediate Similarity NPC61688
0.7684 Intermediate Similarity NPC253586
0.7684 Intermediate Similarity NPC472145
0.7683 Intermediate Similarity NPC476718
0.7674 Intermediate Similarity NPC1882
0.766 Intermediate Similarity NPC82633
0.7653 Intermediate Similarity NPC99510
0.7647 Intermediate Similarity NPC252483
0.7647 Intermediate Similarity NPC191345
0.764 Intermediate Similarity NPC474572
0.764 Intermediate Similarity NPC473350
0.764 Intermediate Similarity NPC476715
0.7634 Intermediate Similarity NPC476189
0.7634 Intermediate Similarity NPC475307
0.7619 Intermediate Similarity NPC474020
0.7609 Intermediate Similarity NPC185529
0.7609 Intermediate Similarity NPC472146
0.7609 Intermediate Similarity NPC18536
0.7609 Intermediate Similarity NPC50443
0.7586 Intermediate Similarity NPC475951
0.7586 Intermediate Similarity NPC328639
0.7586 Intermediate Similarity NPC329490
0.7586 Intermediate Similarity NPC58631
0.7582 Intermediate Similarity NPC470872
0.7582 Intermediate Similarity NPC477614
0.7582 Intermediate Similarity NPC226491
0.7579 Intermediate Similarity NPC163685
0.7579 Intermediate Similarity NPC193785
0.7576 Intermediate Similarity NPC100078
0.7556 Intermediate Similarity NPC228593
0.7556 Intermediate Similarity NPC475729
0.7556 Intermediate Similarity NPC474215
0.7556 Intermediate Similarity NPC235196
0.7556 Intermediate Similarity NPC155531
0.7556 Intermediate Similarity NPC83242
0.7556 Intermediate Similarity NPC471411
0.7556 Intermediate Similarity NPC471410
0.7556 Intermediate Similarity NPC215968
0.7556 Intermediate Similarity NPC477283
0.7553 Intermediate Similarity NPC309127
0.7553 Intermediate Similarity NPC247877
0.7551 Intermediate Similarity NPC471254
0.7528 Intermediate Similarity NPC34984
0.7528 Intermediate Similarity NPC25037
0.7528 Intermediate Similarity NPC237938
0.7528 Intermediate Similarity NPC79308
0.7528 Intermediate Similarity NPC219535
0.7527 Intermediate Similarity NPC474065
0.7526 Intermediate Similarity NPC477655
0.7526 Intermediate Similarity NPC108371
0.7525 Intermediate Similarity NPC207693
0.75 Intermediate Similarity NPC472233
0.75 Intermediate Similarity NPC472234
0.75 Intermediate Similarity NPC286719
0.75 Intermediate Similarity NPC306776
0.75 Intermediate Similarity NPC166079
0.75 Intermediate Similarity NPC472655
0.75 Intermediate Similarity NPC477286
0.7475 Intermediate Similarity NPC471253
0.7475 Intermediate Similarity NPC72842
0.7475 Intermediate Similarity NPC473406
0.7474 Intermediate Similarity NPC17336
0.7474 Intermediate Similarity NPC217329
0.7474 Intermediate Similarity NPC62407
0.7474 Intermediate Similarity NPC287354
0.7473 Intermediate Similarity NPC239938
0.7471 Intermediate Similarity NPC60568
0.7451 Intermediate Similarity NPC22709
0.7449 Intermediate Similarity NPC178853
0.7449 Intermediate Similarity NPC98225
0.7447 Intermediate Similarity NPC228700
0.7444 Intermediate Similarity NPC131350
0.7444 Intermediate Similarity NPC477205
0.7444 Intermediate Similarity NPC235402
0.7419 Intermediate Similarity NPC88337
0.7419 Intermediate Similarity NPC475211
0.7419 Intermediate Similarity NPC475776
0.7416 Intermediate Similarity NPC268578
0.7416 Intermediate Similarity NPC292458
0.7416 Intermediate Similarity NPC217559
0.7416 Intermediate Similarity NPC111582
0.7416 Intermediate Similarity NPC477285
0.7412 Intermediate Similarity NPC136424
0.7412 Intermediate Similarity NPC471046
0.7407 Intermediate Similarity NPC119838
0.74 Intermediate Similarity NPC283850
0.7396 Intermediate Similarity NPC473964
0.7391 Intermediate Similarity NPC473319
0.7391 Intermediate Similarity NPC131104
0.7391 Intermediate Similarity NPC3032
0.7386 Intermediate Similarity NPC211049
0.7386 Intermediate Similarity NPC280781
0.7386 Intermediate Similarity NPC190940
0.7386 Intermediate Similarity NPC48756
0.7386 Intermediate Similarity NPC116320
0.7386 Intermediate Similarity NPC119922
0.7381 Intermediate Similarity NPC96759
0.7374 Intermediate Similarity NPC470172
0.7374 Intermediate Similarity NPC80640
0.7368 Intermediate Similarity NPC206878
0.7363 Intermediate Similarity NPC80700
0.7363 Intermediate Similarity NPC92139
0.7356 Intermediate Similarity NPC80891
0.7356 Intermediate Similarity NPC201276
0.7347 Intermediate Similarity NPC80417
0.734 Intermediate Similarity NPC165180
0.7333 Intermediate Similarity NPC475689
0.7333 Intermediate Similarity NPC319909
0.7326 Intermediate Similarity NPC476719
0.732 Intermediate Similarity NPC469810
0.732 Intermediate Similarity NPC473963
0.732 Intermediate Similarity NPC474921
0.7312 Intermediate Similarity NPC471043

  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 NPC65133 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
0.7629 Intermediate Similarity NPD1700 Approved
0.7407 Intermediate Similarity NPD229 Approved
0.7241 Intermediate Similarity NPD6118 Approved
0.7241 Intermediate Similarity NPD6115 Approved
0.7241 Intermediate Similarity NPD6114 Approved
0.7241 Intermediate Similarity NPD6697 Approved
0.7184 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6116 Phase 1
0.7037 Intermediate Similarity NPD9496 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6117 Approved
0.7 Intermediate Similarity NPD1779 Approved
0.7 Intermediate Similarity NPD1780 Approved
0.6941 Remote Similarity NPD5777 Approved
0.6923 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6782 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6729 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6008 Approved
0.6636 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6633 Remote Similarity NPD8034 Phase 2
0.6633 Remote Similarity NPD8035 Phase 2
0.6571 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6517 Remote Similarity NPD3702 Approved
0.6517 Remote Similarity NPD3703 Phase 2
0.6489 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6489 Remote Similarity NPD3669 Approved
0.6481 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6435 Remote Similarity NPD6921 Approved
0.641 Remote Similarity NPD7492 Approved
0.6372 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6356 Remote Similarity NPD6616 Approved
0.6348 Remote Similarity NPD6059 Approved
0.6348 Remote Similarity NPD6054 Approved
0.6337 Remote Similarity NPD7900 Approved
0.6337 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6322 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6322 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7078 Approved
0.6303 Remote Similarity NPD8293 Discontinued
0.6275 Remote Similarity NPD6356 Clinical (unspecified phase)
0.625 Remote Similarity NPD8133 Approved
0.625 Remote Similarity NPD4225 Approved
0.625 Remote Similarity NPD7736 Approved
0.6239 Remote Similarity NPD6370 Approved
0.6238 Remote Similarity NPD6399 Phase 3
0.6207 Remote Similarity NPD5360 Phase 3
0.6207 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6207 Remote Similarity NPD6319 Approved
0.6186 Remote Similarity NPD7520 Clinical (unspecified phase)
0.618 Remote Similarity NPD6081 Approved
0.617 Remote Similarity NPD6928 Phase 2
0.6163 Remote Similarity NPD4224 Phase 2
0.6154 Remote Similarity NPD6016 Approved
0.6154 Remote Similarity NPD7902 Approved
0.6154 Remote Similarity NPD6015 Approved
0.6136 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6129 Remote Similarity NPD4802 Phase 2
0.6129 Remote Similarity NPD4238 Approved
0.6111 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6111 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6102 Remote Similarity NPD5988 Approved
0.6095 Remote Similarity NPD7638 Approved
0.6091 Remote Similarity NPD7320 Approved
0.6087 Remote Similarity NPD7115 Discovery
0.6078 Remote Similarity NPD8171 Discontinued
0.6067 Remote Similarity NPD4245 Approved
0.6067 Remote Similarity NPD2687 Approved
0.6067 Remote Similarity NPD2254 Approved
0.6067 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6067 Remote Similarity NPD2686 Approved
0.6067 Remote Similarity NPD4244 Approved
0.6066 Remote Similarity NPD7319 Approved
0.6055 Remote Similarity NPD6675 Approved
0.6055 Remote Similarity NPD6402 Approved
0.6055 Remote Similarity NPD7128 Approved
0.6055 Remote Similarity NPD5739 Approved
0.605 Remote Similarity NPD8328 Phase 3
0.6047 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6038 Remote Similarity NPD7640 Approved
0.6038 Remote Similarity NPD7639 Approved
0.6036 Remote Similarity NPD6372 Approved
0.6036 Remote Similarity NPD6373 Approved
0.6019 Remote Similarity NPD7748 Approved
0.6018 Remote Similarity NPD8297 Approved
0.6 Remote Similarity NPD6903 Approved
0.6 Remote Similarity NPD6940 Discontinued
0.5965 Remote Similarity NPD4632 Approved
0.596 Remote Similarity NPD7334 Approved
0.596 Remote Similarity NPD5330 Approved
0.596 Remote Similarity NPD6684 Approved
0.596 Remote Similarity NPD6409 Approved
0.596 Remote Similarity NPD7146 Approved
0.596 Remote Similarity NPD7521 Approved
0.5955 Remote Similarity NPD3698 Phase 2
0.595 Remote Similarity NPD7507 Approved
0.5946 Remote Similarity NPD6686 Approved
0.5946 Remote Similarity NPD6899 Approved
0.5946 Remote Similarity NPD6881 Approved
0.593 Remote Similarity NPD371 Approved
0.5929 Remote Similarity NPD6649 Approved
0.5929 Remote Similarity NPD6650 Approved
0.5926 Remote Similarity NPD7632 Discontinued
0.5889 Remote Similarity NPD4789 Approved
0.5888 Remote Similarity NPD8418 Phase 2
0.5865 Remote Similarity NPD6001 Approved
0.5865 Remote Similarity NPD5282 Discontinued
0.5859 Remote Similarity NPD1694 Approved
0.5856 Remote Similarity NPD5697 Approved
0.5856 Remote Similarity NPD6412 Phase 2
0.5856 Remote Similarity NPD5701 Approved
0.5854 Remote Similarity NPD6033 Approved
0.5842 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5842 Remote Similarity NPD5737 Approved
0.5842 Remote Similarity NPD6672 Approved
0.5841 Remote Similarity NPD6883 Approved
0.5841 Remote Similarity NPD7102 Approved
0.5841 Remote Similarity NPD7290 Approved
0.5825 Remote Similarity NPD7515 Phase 2
0.5824 Remote Similarity NPD4758 Discontinued
0.5812 Remote Similarity NPD6009 Approved
0.5789 Remote Similarity NPD3671 Phase 1
0.5789 Remote Similarity NPD6847 Approved
0.5789 Remote Similarity NPD5364 Discontinued
0.5789 Remote Similarity NPD8130 Phase 1
0.5789 Remote Similarity NPD6617 Approved
0.5789 Remote Similarity NPD6869 Approved
0.5785 Remote Similarity NPD7604 Phase 2
0.5778 Remote Similarity NPD3725 Approved
0.5778 Remote Similarity NPD3726 Approved
0.5763 Remote Similarity NPD7328 Approved
0.5763 Remote Similarity NPD7327 Approved
0.5752 Remote Similarity NPD6014 Approved
0.5752 Remote Similarity NPD6012 Approved
0.5752 Remote Similarity NPD6013 Approved
0.575 Remote Similarity NPD5983 Phase 2
0.5743 Remote Similarity NPD3573 Approved
0.5739 Remote Similarity NPD6882 Approved
0.5714 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7516 Approved
0.5714 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5702 Remote Similarity NPD4634 Approved
0.5701 Remote Similarity NPD6083 Phase 2
0.5701 Remote Similarity NPD6084 Phase 2
0.5699 Remote Similarity NPD1811 Approved
0.5699 Remote Similarity NPD1810 Approved
0.5691 Remote Similarity NPD6336 Discontinued
0.5686 Remote Similarity NPD4264 Clinical (unspecified phase)
0.5673 Remote Similarity NPD6411 Approved
0.5664 Remote Similarity NPD6011 Approved
0.5656 Remote Similarity NPD6067 Discontinued
0.5652 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5648 Remote Similarity NPD5696 Approved
0.5644 Remote Similarity NPD3618 Phase 1
0.5644 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5644 Remote Similarity NPD6098 Approved
0.5641 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5636 Remote Similarity NPD8083 Approved
0.5636 Remote Similarity NPD8084 Approved
0.5636 Remote Similarity NPD8138 Approved
0.5636 Remote Similarity NPD8082 Approved
0.5636 Remote Similarity NPD8086 Approved
0.5636 Remote Similarity NPD8085 Approved
0.5636 Remote Similarity NPD8139 Approved
0.5631 Remote Similarity NPD6904 Approved
0.5631 Remote Similarity NPD6080 Approved
0.5631 Remote Similarity NPD6673 Approved
0.562 Remote Similarity NPD8516 Approved
0.562 Remote Similarity NPD8517 Approved
0.562 Remote Similarity NPD8515 Approved
0.562 Remote Similarity NPD8513 Phase 3
0.5619 Remote Similarity NPD5778 Approved
0.5619 Remote Similarity NPD5779 Approved
0.561 Remote Similarity NPD3729 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data