Structure

Physi-Chem Properties

Molecular Weight:  358.21
Volume:  379.457
LogP:  3.157
LogD:  3.206
LogS:  -4.442
# Rotatable Bonds:  0
TPSA:  71.44
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.533
Synthetic Accessibility Score:  4.767
Fsp3:  0.773
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.992
MDCK Permeability:  3.745638969121501e-05
Pgp-inhibitor:  0.99
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.025
30% Bioavailability (F30%):  0.301

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.057
Plasma Protein Binding (PPB):  75.02245330810547%
Volume Distribution (VD):  0.602
Pgp-substrate:  14.416472434997559%

ADMET: Metabolism

CYP1A2-inhibitor:  0.041
CYP1A2-substrate:  0.747
CYP2C19-inhibitor:  0.18
CYP2C19-substrate:  0.838
CYP2C9-inhibitor:  0.265
CYP2C9-substrate:  0.143
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.354
CYP3A4-inhibitor:  0.457
CYP3A4-substrate:  0.308

ADMET: Excretion

Clearance (CL):  4.956
Half-life (T1/2):  0.212

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.024
Drug-inuced Liver Injury (DILI):  0.062
AMES Toxicity:  0.047
Rat Oral Acute Toxicity:  0.403
Maximum Recommended Daily Dose:  0.952
Skin Sensitization:  0.129
Carcinogencity:  0.017
Eye Corrosion:  0.017
Eye Irritation:  0.168
Respiratory Toxicity:  0.878

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  Natural Product: NPC280725

Natural Product ID:  NPC280725
Common Name*:   Palbinone
IUPAC Name:   (3S,5R,8R,9R,10S,14S)-3,17-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9-hexahydro-1H-cyclopenta[a]phenanthrene-15,16-dione
Synonyms:   Palbinone
Standard InCHIKey:  KIAKLFLISZCITK-PPAUHQMUSA-N
Standard InCHI:  InChI=1S/C22H30O4/c1-19(2)13-8-11-21(4)14(20(13,3)10-9-15(19)23)7-6-12-16(24)17(25)18(26)22(12,21)5/h6-7,13-15,23-24H,8-11H2,1-5H3/t13-,14+,15-,20-,21+,22-/m0/s1
SMILES:  CC1(C)[C@@H]2CC[C@]3(C)[C@H](C=CC4=C(C(=O)C(=O)[C@@]34C)O)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL575924
PubChem CID:   9841735
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001194] Oxosteroids
          • [CHEMONTID:0003060] 16-oxosteroids

*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
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Anhui province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Gansu province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Henan province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shandong province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shanxi province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. DOI[10.2174/092986712800229032]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. PMID[11339628]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. bark n.a. PMID[17260795]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. PMID[19402674]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. Daejeon, Korea 2007-Jan PMID[19670875]
NPO30226 Paeonia albiflora Species Paeoniaceae Eukaryota roots n.a. n.a. PMID[19691309]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19721258]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19772486]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[20806783]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[20822014]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21782011]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21954959]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota roots Whitessence Srl, Viterbo, Italy 2005-OCT PMID[21954959]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[22190295]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. root n.a. PMID[22547314]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota root bark Bozhou, Anhui Province, China 2010-AUG PMID[24377852]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. flower n.a. PMID[24504864]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota Flowers LuoYang, HeNan, China n.a. PMID[24621197]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[26838074]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27313650]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27429639]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[29741372]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds DingXi, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds LanZhou, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds HeZe, ShanDong, China early autumn (from August to the beginning of September PMID[32545196]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[32951423]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Xinjiang,China PMID[33063333]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO30226 Paeonia albiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21458 Radix paeoniae rubra Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30226 Paeonia albiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22550 Paeonia suffruticosa Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9798 Paeonia lactiflora Species Paeoniaceae 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
NPT65 Cell Line HepG2 Homo sapiens Survival = 41.6 % PMID[501561]
NPT65 Cell Line HepG2 Homo sapiens Survival = 81.5 % PMID[501561]
NPT65 Cell Line HepG2 Homo sapiens Survival = 99.8 % PMID[501561]
NPT65 Cell Line HepG2 Homo sapiens Survival = 98.7 % PMID[501561]
NPT68 Individual Protein Aldose reductase Rattus norvegicus IC50 = 11400.0 nM PMID[501562]
NPT35 Others n.a. IC50 > 500000.0 nM PMID[501562]

☑ 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 NPC280725 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
0.8936 High Similarity NPC473161
0.8804 High Similarity NPC185936
0.8804 High Similarity NPC168027
0.8778 High Similarity NPC141292
0.8723 High Similarity NPC88310
0.871 High Similarity NPC134826
0.8681 High Similarity NPC292491
0.8681 High Similarity NPC310752
0.8632 High Similarity NPC471153
0.8617 High Similarity NPC196485
0.8617 High Similarity NPC245972
0.8617 High Similarity NPC474328
0.8587 High Similarity NPC119416
0.8556 High Similarity NPC470574
0.8511 High Similarity NPC211230
0.8495 Intermediate Similarity NPC129913
0.8495 Intermediate Similarity NPC85173
0.8478 Intermediate Similarity NPC328539
0.8462 Intermediate Similarity NPC327115
0.8462 Intermediate Similarity NPC94666
0.8444 Intermediate Similarity NPC237712
0.8438 Intermediate Similarity NPC192428
0.8427 Intermediate Similarity NPC48362
0.8421 Intermediate Similarity NPC474690
0.8421 Intermediate Similarity NPC49670
0.8421 Intermediate Similarity NPC473172
0.8421 Intermediate Similarity NPC23170
0.8421 Intermediate Similarity NPC299100
0.8404 Intermediate Similarity NPC272746
0.8387 Intermediate Similarity NPC31985
0.8387 Intermediate Similarity NPC474245
0.8387 Intermediate Similarity NPC1015
0.837 Intermediate Similarity NPC475740
0.837 Intermediate Similarity NPC58063
0.837 Intermediate Similarity NPC136548
0.8367 Intermediate Similarity NPC144956
0.8352 Intermediate Similarity NPC32037
0.8351 Intermediate Similarity NPC18509
0.8333 Intermediate Similarity NPC473170
0.8333 Intermediate Similarity NPC180950
0.8316 Intermediate Similarity NPC475255
0.8316 Intermediate Similarity NPC12722
0.8315 Intermediate Similarity NPC14151
0.8315 Intermediate Similarity NPC121984
0.8298 Intermediate Similarity NPC126993
0.8283 Intermediate Similarity NPC282524
0.828 Intermediate Similarity NPC474677
0.828 Intermediate Similarity NPC471722
0.828 Intermediate Similarity NPC471724
0.8265 Intermediate Similarity NPC103051
0.8265 Intermediate Similarity NPC191565
0.8261 Intermediate Similarity NPC31564
0.8261 Intermediate Similarity NPC474733
0.8261 Intermediate Similarity NPC474778
0.8261 Intermediate Similarity NPC194417
0.8261 Intermediate Similarity NPC145879
0.8261 Intermediate Similarity NPC474732
0.8261 Intermediate Similarity NPC20688
0.8261 Intermediate Similarity NPC51014
0.8261 Intermediate Similarity NPC72133
0.8247 Intermediate Similarity NPC473164
0.8247 Intermediate Similarity NPC250757
0.8247 Intermediate Similarity NPC301534
0.8242 Intermediate Similarity NPC161423
0.8242 Intermediate Similarity NPC58841
0.8242 Intermediate Similarity NPC227064
0.8242 Intermediate Similarity NPC85774
0.8242 Intermediate Similarity NPC321187
0.8242 Intermediate Similarity NPC329043
0.8242 Intermediate Similarity NPC214043
0.8229 Intermediate Similarity NPC473162
0.8229 Intermediate Similarity NPC471207
0.8229 Intermediate Similarity NPC8993
0.8229 Intermediate Similarity NPC111015
0.8222 Intermediate Similarity NPC103486
0.8222 Intermediate Similarity NPC151519
0.8218 Intermediate Similarity NPC213366
0.8211 Intermediate Similarity NPC475806
0.8211 Intermediate Similarity NPC473998
0.8211 Intermediate Similarity NPC212301
0.8211 Intermediate Similarity NPC110657
0.8211 Intermediate Similarity NPC86266
0.8211 Intermediate Similarity NPC131872
0.8211 Intermediate Similarity NPC473167
0.8211 Intermediate Similarity NPC19114
0.8191 Intermediate Similarity NPC473999
0.8191 Intermediate Similarity NPC86319
0.8191 Intermediate Similarity NPC310010
0.8191 Intermediate Similarity NPC275740
0.8191 Intermediate Similarity NPC309603
0.8191 Intermediate Similarity NPC326627
0.8182 Intermediate Similarity NPC35751
0.8172 Intermediate Similarity NPC298904
0.8172 Intermediate Similarity NPC272039
0.8172 Intermediate Similarity NPC220930
0.8163 Intermediate Similarity NPC474785
0.8163 Intermediate Similarity NPC108078
0.8163 Intermediate Similarity NPC474938
0.8152 Intermediate Similarity NPC197823
0.8152 Intermediate Similarity NPC79573
0.8144 Intermediate Similarity NPC148523
0.8144 Intermediate Similarity NPC139459
0.8125 Intermediate Similarity NPC107674
0.8125 Intermediate Similarity NPC141497
0.8125 Intermediate Similarity NPC474807
0.8125 Intermediate Similarity NPC170220
0.8119 Intermediate Similarity NPC247957
0.8119 Intermediate Similarity NPC249187
0.8119 Intermediate Similarity NPC475050
0.8111 Intermediate Similarity NPC225515
0.8111 Intermediate Similarity NPC116797
0.8105 Intermediate Similarity NPC48010
0.8105 Intermediate Similarity NPC191684
0.8095 Intermediate Similarity NPC207689
0.809 Intermediate Similarity NPC474113
0.8085 Intermediate Similarity NPC472802
0.8085 Intermediate Similarity NPC158778
0.8085 Intermediate Similarity NPC230387
0.8085 Intermediate Similarity NPC131470
0.8085 Intermediate Similarity NPC53911
0.8085 Intermediate Similarity NPC143767
0.8085 Intermediate Similarity NPC328313
0.8081 Intermediate Similarity NPC108368
0.8081 Intermediate Similarity NPC114274
0.8081 Intermediate Similarity NPC57079
0.8081 Intermediate Similarity NPC147954
0.8068 Intermediate Similarity NPC197659
0.8065 Intermediate Similarity NPC471737
0.8065 Intermediate Similarity NPC475022
0.8065 Intermediate Similarity NPC222613
0.8065 Intermediate Similarity NPC472985
0.8065 Intermediate Similarity NPC158393
0.8065 Intermediate Similarity NPC472986
0.8065 Intermediate Similarity NPC118648
0.8061 Intermediate Similarity NPC249954
0.8061 Intermediate Similarity NPC328162
0.8061 Intermediate Similarity NPC98874
0.8061 Intermediate Similarity NPC117133
0.8061 Intermediate Similarity NPC305483
0.8061 Intermediate Similarity NPC96859
0.8061 Intermediate Similarity NPC167193
0.8061 Intermediate Similarity NPC472806
0.8043 Intermediate Similarity NPC473246
0.8043 Intermediate Similarity NPC59453
0.8043 Intermediate Similarity NPC221758
0.8041 Intermediate Similarity NPC473280
0.8041 Intermediate Similarity NPC473431
0.8041 Intermediate Similarity NPC471078
0.8041 Intermediate Similarity NPC473435
0.8041 Intermediate Similarity NPC474882
0.8041 Intermediate Similarity NPC209662
0.8021 Intermediate Similarity NPC65120
0.8021 Intermediate Similarity NPC155304
0.8021 Intermediate Similarity NPC474525
0.8021 Intermediate Similarity NPC99380
0.8021 Intermediate Similarity NPC233455
0.8021 Intermediate Similarity NPC145067
0.8021 Intermediate Similarity NPC158030
0.8021 Intermediate Similarity NPC4036
0.8 Intermediate Similarity NPC474704
0.8 Intermediate Similarity NPC84271
0.8 Intermediate Similarity NPC2482
0.8 Intermediate Similarity NPC32830
0.8 Intermediate Similarity NPC65615
0.8 Intermediate Similarity NPC477943
0.8 Intermediate Similarity NPC475921
0.8 Intermediate Similarity NPC46761
0.8 Intermediate Similarity NPC229871
0.8 Intermediate Similarity NPC76879
0.8 Intermediate Similarity NPC235077
0.8 Intermediate Similarity NPC469319
0.8 Intermediate Similarity NPC68148
0.8 Intermediate Similarity NPC266955
0.8 Intermediate Similarity NPC77168
0.8 Intermediate Similarity NPC186688
0.8 Intermediate Similarity NPC26959
0.8 Intermediate Similarity NPC69627
0.8 Intermediate Similarity NPC102414
0.8 Intermediate Similarity NPC268406
0.8 Intermediate Similarity NPC476809
0.798 Intermediate Similarity NPC89225
0.798 Intermediate Similarity NPC273269
0.798 Intermediate Similarity NPC21728
0.7979 Intermediate Similarity NPC93778
0.7979 Intermediate Similarity NPC474684
0.7979 Intermediate Similarity NPC96496
0.7979 Intermediate Similarity NPC142361
0.7978 Intermediate Similarity NPC178852
0.7978 Intermediate Similarity NPC476808
0.7961 Intermediate Similarity NPC32006
0.7961 Intermediate Similarity NPC85529
0.7961 Intermediate Similarity NPC257353
0.7961 Intermediate Similarity NPC266570
0.7961 Intermediate Similarity NPC166607
0.7959 Intermediate Similarity NPC259286
0.7959 Intermediate Similarity NPC271195
0.7959 Intermediate Similarity NPC472485
0.7957 Intermediate Similarity NPC6185
0.7957 Intermediate Similarity NPC469948
0.7957 Intermediate Similarity NPC133954

  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 NPC280725 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
0.8667 High Similarity NPD3618 Phase 1
0.8632 High Similarity NPD5222 Approved
0.8632 High Similarity NPD5221 Approved
0.8632 High Similarity NPD5220 Clinical (unspecified phase)
0.8542 High Similarity NPD5173 Approved
0.8462 Intermediate Similarity NPD5279 Phase 3
0.8438 Intermediate Similarity NPD4697 Phase 3
0.8404 Intermediate Similarity NPD6079 Approved
0.8387 Intermediate Similarity NPD5328 Approved
0.8367 Intermediate Similarity NPD4696 Approved
0.8367 Intermediate Similarity NPD5286 Approved
0.8367 Intermediate Similarity NPD5285 Approved
0.8351 Intermediate Similarity NPD4755 Approved
0.8283 Intermediate Similarity NPD5223 Approved
0.8242 Intermediate Similarity NPD3133 Approved
0.8242 Intermediate Similarity NPD3666 Approved
0.8242 Intermediate Similarity NPD3665 Phase 1
0.8222 Intermediate Similarity NPD3667 Approved
0.82 Intermediate Similarity NPD4633 Approved
0.82 Intermediate Similarity NPD5225 Approved
0.82 Intermediate Similarity NPD5224 Approved
0.82 Intermediate Similarity NPD5226 Approved
0.82 Intermediate Similarity NPD5211 Phase 2
0.8191 Intermediate Similarity NPD4753 Phase 2
0.8182 Intermediate Similarity NPD4700 Approved
0.8125 Intermediate Similarity NPD4202 Approved
0.8119 Intermediate Similarity NPD5175 Approved
0.8119 Intermediate Similarity NPD5174 Approved
0.8065 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.8043 Intermediate Similarity NPD4786 Approved
0.8039 Intermediate Similarity NPD5141 Approved
0.8021 Intermediate Similarity NPD7515 Phase 2
0.8 Intermediate Similarity NPD4695 Discontinued
0.8 Intermediate Similarity NPD4634 Approved
0.7978 Intermediate Similarity NPD3617 Approved
0.7959 Intermediate Similarity NPD4629 Approved
0.7959 Intermediate Similarity NPD5210 Approved
0.7941 Intermediate Similarity NPD4754 Approved
0.7885 Intermediate Similarity NPD5697 Approved
0.7872 Intermediate Similarity NPD5280 Approved
0.7872 Intermediate Similarity NPD4694 Approved
0.7849 Intermediate Similarity NPD4197 Approved
0.781 Intermediate Similarity NPD4729 Approved
0.781 Intermediate Similarity NPD6011 Approved
0.781 Intermediate Similarity NPD6881 Approved
0.781 Intermediate Similarity NPD4730 Approved
0.781 Intermediate Similarity NPD6899 Approved
0.781 Intermediate Similarity NPD5168 Approved
0.7788 Intermediate Similarity NPD7128 Approved
0.7788 Intermediate Similarity NPD4767 Approved
0.7788 Intermediate Similarity NPD4768 Approved
0.7788 Intermediate Similarity NPD5739 Approved
0.7788 Intermediate Similarity NPD6675 Approved
0.7788 Intermediate Similarity NPD6402 Approved
0.7766 Intermediate Similarity NPD5329 Approved
0.7736 Intermediate Similarity NPD6012 Approved
0.7736 Intermediate Similarity NPD6014 Approved
0.7736 Intermediate Similarity NPD6013 Approved
0.7714 Intermediate Similarity NPD5701 Approved
0.7684 Intermediate Similarity NPD5690 Phase 2
0.7677 Intermediate Similarity NPD7748 Approved
0.7664 Intermediate Similarity NPD7102 Approved
0.7664 Intermediate Similarity NPD5169 Approved
0.7664 Intermediate Similarity NPD5247 Approved
0.7664 Intermediate Similarity NPD5251 Approved
0.7664 Intermediate Similarity NPD6883 Approved
0.7664 Intermediate Similarity NPD5135 Approved
0.7664 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD7290 Approved
0.7664 Intermediate Similarity NPD5250 Approved
0.7664 Intermediate Similarity NPD5249 Phase 3
0.7664 Intermediate Similarity NPD5248 Approved
0.766 Intermediate Similarity NPD3668 Phase 3
0.7642 Intermediate Similarity NPD5128 Approved
0.7642 Intermediate Similarity NPD7320 Approved
0.7634 Intermediate Similarity NPD4223 Phase 3
0.7634 Intermediate Similarity NPD4221 Approved
0.7629 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD6084 Phase 2
0.7624 Intermediate Similarity NPD6083 Phase 2
0.7609 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD6649 Approved
0.7593 Intermediate Similarity NPD5215 Approved
0.7593 Intermediate Similarity NPD8130 Phase 1
0.7593 Intermediate Similarity NPD5216 Approved
0.7593 Intermediate Similarity NPD5127 Approved
0.7593 Intermediate Similarity NPD6847 Approved
0.7593 Intermediate Similarity NPD5217 Approved
0.7593 Intermediate Similarity NPD6650 Approved
0.7593 Intermediate Similarity NPD6869 Approved
0.7593 Intermediate Similarity NPD6617 Approved
0.757 Intermediate Similarity NPD6372 Approved
0.757 Intermediate Similarity NPD6373 Approved
0.7526 Intermediate Similarity NPD6672 Approved
0.7526 Intermediate Similarity NPD5737 Approved
0.7523 Intermediate Similarity NPD6882 Approved
0.7523 Intermediate Similarity NPD8297 Approved
0.75 Intermediate Similarity NPD4623 Approved
0.75 Intermediate Similarity NPD4519 Discontinued
0.7475 Intermediate Similarity NPD5281 Approved
0.7475 Intermediate Similarity NPD5284 Approved
0.7455 Intermediate Similarity NPD4632 Approved
0.7451 Intermediate Similarity NPD7902 Approved
0.7431 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD5695 Phase 3
0.74 Intermediate Similarity NPD6399 Phase 3
0.7387 Intermediate Similarity NPD5167 Approved
0.7379 Intermediate Similarity NPD5696 Approved
0.7368 Intermediate Similarity NPD6319 Approved
0.7368 Intermediate Similarity NPD6054 Approved
0.7333 Intermediate Similarity NPD4058 Approved
0.7321 Intermediate Similarity NPD6868 Approved
0.732 Intermediate Similarity NPD7334 Approved
0.732 Intermediate Similarity NPD6409 Approved
0.732 Intermediate Similarity NPD7521 Approved
0.732 Intermediate Similarity NPD6684 Approved
0.732 Intermediate Similarity NPD4693 Phase 3
0.732 Intermediate Similarity NPD4690 Approved
0.732 Intermediate Similarity NPD5330 Approved
0.732 Intermediate Similarity NPD4138 Approved
0.732 Intermediate Similarity NPD4689 Approved
0.732 Intermediate Similarity NPD5205 Approved
0.732 Intermediate Similarity NPD4688 Approved
0.732 Intermediate Similarity NPD7146 Approved
0.7304 Intermediate Similarity NPD6015 Approved
0.7304 Intermediate Similarity NPD6016 Approved
0.73 Intermediate Similarity NPD6411 Approved
0.73 Intermediate Similarity NPD5694 Approved
0.7257 Intermediate Similarity NPD6009 Approved
0.7257 Intermediate Similarity NPD6317 Approved
0.7257 Intermediate Similarity NPD7115 Discovery
0.7241 Intermediate Similarity NPD5988 Approved
0.7241 Intermediate Similarity NPD6370 Approved
0.7234 Intermediate Similarity NPD7525 Registered
0.7228 Intermediate Similarity NPD5133 Approved
0.7217 Intermediate Similarity NPD6059 Approved
0.7216 Intermediate Similarity NPD1696 Phase 3
0.7216 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7638 Approved
0.72 Intermediate Similarity NPD5692 Phase 3
0.7193 Intermediate Similarity NPD6313 Approved
0.7193 Intermediate Similarity NPD6314 Approved
0.7193 Intermediate Similarity NPD6335 Approved
0.7188 Intermediate Similarity NPD4788 Approved
0.7174 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD6903 Approved
0.7172 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6274 Approved
0.7157 Intermediate Similarity NPD5282 Discontinued
0.7157 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD7900 Approved
0.7143 Intermediate Similarity NPD7640 Approved
0.7143 Intermediate Similarity NPD7639 Approved
0.7143 Intermediate Similarity NPD4687 Approved
0.713 Intermediate Similarity NPD7101 Approved
0.713 Intermediate Similarity NPD7100 Approved
0.7129 Intermediate Similarity NPD6050 Approved
0.7128 Intermediate Similarity NPD4195 Approved
0.7119 Intermediate Similarity NPD7492 Approved
0.71 Intermediate Similarity NPD6904 Approved
0.71 Intermediate Similarity NPD6101 Approved
0.71 Intermediate Similarity NPD6080 Approved
0.71 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD6673 Approved
0.7079 Intermediate Similarity NPD4137 Phase 3
0.7071 Intermediate Similarity NPD3573 Approved
0.7065 Intermediate Similarity NPD6942 Approved
0.7065 Intermediate Similarity NPD7339 Approved
0.7059 Intermediate Similarity NPD6616 Approved
0.7048 Intermediate Similarity NPD5290 Discontinued
0.703 Intermediate Similarity NPD4096 Approved
0.7009 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD5983 Phase 2
0.7009 Intermediate Similarity NPD5091 Approved
0.7 Intermediate Similarity NPD4747 Approved
0.7 Intermediate Similarity NPD4691 Approved
0.7 Intermediate Similarity NPD4518 Approved
0.7 Intermediate Similarity NPD7078 Approved
0.6983 Remote Similarity NPD4522 Approved
0.6961 Remote Similarity NPD5693 Phase 1
0.6957 Remote Similarity NPD5733 Approved
0.6947 Remote Similarity NPD7645 Phase 2
0.6942 Remote Similarity NPD7736 Approved
0.6923 Remote Similarity NPD5276 Approved
0.6923 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6909 Remote Similarity NPD6412 Phase 2
0.6891 Remote Similarity NPD7604 Phase 2
0.6889 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6887 Remote Similarity NPD4225 Approved
0.6864 Remote Similarity NPD6909 Approved
0.6864 Remote Similarity NPD6908 Approved
0.6863 Remote Similarity NPD5207 Approved
0.686 Remote Similarity NPD8293 Discontinued
0.6818 Remote Similarity NPD6008 Approved
0.6803 Remote Similarity NPD6033 Approved
0.68 Remote Similarity NPD6098 Approved
0.6796 Remote Similarity NPD8034 Phase 2
0.6796 Remote Similarity NPD8035 Phase 2
0.6777 Remote Similarity NPD6336 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