Structure

Physi-Chem Properties

Molecular Weight:  580.14
Volume:  573.704
LogP:  6.637
LogD:  2.725
LogS:  -5.716
# Rotatable Bonds:  6
TPSA:  148.8
# H-Bond Aceptor:  10
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.213
Synthetic Accessibility Score:  2.971
Fsp3:  0.091
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.98
MDCK Permeability:  2.8769347409252077e-05
Pgp-inhibitor:  0.978
Pgp-substrate:  0.066
Human Intestinal Absorption (HIA):  0.106
20% Bioavailability (F20%):  0.026
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  91.53190612792969%
Volume Distribution (VD):  0.389
Pgp-substrate:  9.507492065429688%

ADMET: Metabolism

CYP1A2-inhibitor:  0.75
CYP1A2-substrate:  0.872
CYP2C19-inhibitor:  0.737
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.696
CYP2C9-substrate:  0.956
CYP2D6-inhibitor:  0.054
CYP2D6-substrate:  0.947
CYP3A4-inhibitor:  0.24
CYP3A4-substrate:  0.14

ADMET: Excretion

Clearance (CL):  3.803
Half-life (T1/2):  0.083

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.423
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.292
Rat Oral Acute Toxicity:  0.029
Maximum Recommended Daily Dose:  0.912
Skin Sensitization:  0.31
Carcinogencity:  0.03
Eye Corrosion:  0.003
Eye Irritation:  0.613
Respiratory Toxicity:  0.124

Download Data

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

  Natural Product: NPC18699

Natural Product ID:  NPC18699
Common Name*:   5,7-Dihydroxy-8-[2-(5-Hydroxy-7-Methoxy-4-Oxochromen-2-Yl)-5-Methoxyphenyl]-2-(4-Methoxyphenyl)Chromen-4-One
IUPAC Name:   5,7-dihydroxy-8-[2-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-5-methoxyphenyl]-2-(4-methoxyphenyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  LDDWBTHCKGZOCL-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C33H24O10/c1-39-17-6-4-16(5-7-17)27-14-26(38)32-24(36)13-23(35)30(33(32)43-27)21-10-18(40-2)8-9-20(21)28-15-25(37)31-22(34)11-19(41-3)12-29(31)42-28/h4-15,34-36H,1-3H3
SMILES:  COc1ccc(c(c1)c1c(O)cc(c2c1oc(cc2=O)c1ccc(cc1)OC)O)c1cc(=O)c2c(o1)cc(cc2O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL316312
PubChem CID:   44327242
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO31343 Taxus chinensis Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[12217376]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[12217376]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota wood n.a. n.a. PMID[12444707]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. xylem n.a. PMID[21138310]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota wood Yunnang Province, China 2000-OCT PMID[21138310]
NPO31343 Taxus chinensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31343 Taxus chinensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT1178 Cell Line KB 3-1 Homo sapiens ED50 > 20.0 ug ml-1 PMID[485416]
NPT1178 Cell Line KB 3-1 Homo sapiens Inhibition = 9.0 % PMID[485416]
NPT81 Cell Line A549 Homo sapiens ED50 > 20.0 ug ml-1 PMID[485416]
NPT81 Cell Line A549 Homo sapiens Inhibition = 58.0 % PMID[485416]
NPT83 Cell Line MCF7 Homo sapiens ED50 > 20.0 ug ml-1 PMID[485416]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 22.0 % PMID[485416]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 > 20.0 ug ml-1 PMID[485416]
NPT147 Cell Line SK-MEL-2 Homo sapiens Inhibition = 9.0 % PMID[485416]
NPT307 Cell Line HOS Homo sapiens ED50 > 20.0 ug ml-1 PMID[485416]
NPT307 Cell Line HOS Homo sapiens Inhibition = 25.0 % PMID[485416]
NPT1535 Cell Line U-87 MG Homo sapiens ED50 > 20.0 ug ml-1 PMID[485416]
NPT1535 Cell Line U-87 MG Homo sapiens Inhibition = 17.0 % PMID[485416]
NPT27 Others Unspecified ED50 > 20.0 ug ml-1 PMID[485416]
NPT27 Others Unspecified Inhibition = 12.0 % PMID[485416]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 20.0 ug ml-1 PMID[485416]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 44.0 % PMID[485416]

☑ 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 NPC18699 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC55443
0.98 High Similarity NPC254351
0.9739 High Similarity NPC273467
0.9739 High Similarity NPC189552
0.9673 High Similarity NPC186325
0.9673 High Similarity NPC312993
0.9669 High Similarity NPC265624
0.9669 High Similarity NPC14606
0.9669 High Similarity NPC52611
0.9669 High Similarity NPC100049
0.9669 High Similarity NPC150908
0.9669 High Similarity NPC205026
0.9669 High Similarity NPC121649
0.9669 High Similarity NPC159707
0.9669 High Similarity NPC248739
0.9669 High Similarity NPC158027
0.9669 High Similarity NPC186227
0.9669 High Similarity NPC215203
0.9608 High Similarity NPC177650
0.9603 High Similarity NPC194593
0.9603 High Similarity NPC72425
0.9603 High Similarity NPC71061
0.9603 High Similarity NPC290830
0.9603 High Similarity NPC303485
0.9551 High Similarity NPC469664
0.947 High Similarity NPC222713
0.947 High Similarity NPC111112
0.947 High Similarity NPC138299
0.947 High Similarity NPC67322
0.9346 High Similarity NPC329844
0.9338 High Similarity NPC288840
0.9338 High Similarity NPC291746
0.9295 High Similarity NPC121647
0.9286 High Similarity NPC66441
0.9286 High Similarity NPC182555
0.9236 High Similarity NPC18380
0.9236 High Similarity NPC301256
0.9236 High Similarity NPC312273
0.9231 High Similarity NPC195167
0.9226 High Similarity NPC54830
0.9226 High Similarity NPC56049
0.9221 High Similarity NPC324447
0.9211 High Similarity NPC100985
0.9211 High Similarity NPC97029
0.9211 High Similarity NPC97028
0.9211 High Similarity NPC288036
0.9211 High Similarity NPC158338
0.9211 High Similarity NPC65589
0.9177 High Similarity NPC473012
0.9177 High Similarity NPC15374
0.9172 High Similarity NPC472060
0.9172 High Similarity NPC472052
0.9172 High Similarity NPC292863
0.9172 High Similarity NPC184326
0.9172 High Similarity NPC470342
0.9167 High Similarity NPC257166
0.9167 High Similarity NPC1796
0.9161 High Similarity NPC300668
0.9161 High Similarity NPC134171
0.9161 High Similarity NPC226656
0.9161 High Similarity NPC66508
0.9156 High Similarity NPC174086
0.9145 High Similarity NPC256672
0.9145 High Similarity NPC27221
0.9145 High Similarity NPC7025
0.9119 High Similarity NPC473009
0.9114 High Similarity NPC137232
0.9108 High Similarity NPC15815
0.9108 High Similarity NPC105584
0.9108 High Similarity NPC51247
0.9108 High Similarity NPC51760
0.9103 High Similarity NPC32867
0.9097 High Similarity NPC169990
0.9097 High Similarity NPC210942
0.9097 High Similarity NPC121568
0.9091 High Similarity NPC474417
0.9091 High Similarity NPC149526
0.9085 High Similarity NPC65775
0.9085 High Similarity NPC216307
0.9085 High Similarity NPC3642
0.9085 High Similarity NPC10027
0.9079 High Similarity NPC22005
0.9079 High Similarity NPC123202
0.9079 High Similarity NPC7943
0.9079 High Similarity NPC261271
0.9079 High Similarity NPC475348
0.9073 High Similarity NPC282957
0.9073 High Similarity NPC194949
0.9062 High Similarity NPC259757
0.9062 High Similarity NPC473010
0.9051 High Similarity NPC42965
0.9051 High Similarity NPC98023
0.9051 High Similarity NPC195136
0.9051 High Similarity NPC226462
0.9045 High Similarity NPC475184
0.9045 High Similarity NPC183
0.9038 High Similarity NPC166054
0.9038 High Similarity NPC55662
0.9038 High Similarity NPC79375
0.9038 High Similarity NPC37253
0.9032 High Similarity NPC78324
0.9032 High Similarity NPC115601
0.9032 High Similarity NPC208011
0.9032 High Similarity NPC39154
0.902 High Similarity NPC106328
0.902 High Similarity NPC122894
0.902 High Similarity NPC35150
0.902 High Similarity NPC152233
0.9006 High Similarity NPC30027
0.9006 High Similarity NPC251336
0.9 High Similarity NPC26238
0.9 High Similarity NPC14871
0.9 High Similarity NPC290160
0.8994 High Similarity NPC472261
0.8987 High Similarity NPC324736
0.8987 High Similarity NPC90497
0.8987 High Similarity NPC295090
0.8981 High Similarity NPC69531
0.8981 High Similarity NPC192587
0.8974 High Similarity NPC95842
0.8974 High Similarity NPC178964
0.8974 High Similarity NPC280530
0.8968 High Similarity NPC232645
0.8968 High Similarity NPC258249
0.8968 High Similarity NPC178484
0.8968 High Similarity NPC72958
0.8968 High Similarity NPC478148
0.8961 High Similarity NPC473978
0.8961 High Similarity NPC329933
0.8954 High Similarity NPC201731
0.8954 High Similarity NPC97716
0.8954 High Similarity NPC104406
0.8954 High Similarity NPC237635
0.8954 High Similarity NPC79469
0.8954 High Similarity NPC24673
0.8954 High Similarity NPC34802
0.8951 High Similarity NPC286230
0.8951 High Similarity NPC253730
0.8947 High Similarity NPC319752
0.8947 High Similarity NPC278175
0.8947 High Similarity NPC257236
0.8944 High Similarity NPC169471
0.894 High Similarity NPC217083
0.894 High Similarity NPC78803
0.894 High Similarity NPC214236
0.894 High Similarity NPC59739
0.894 High Similarity NPC310340
0.894 High Similarity NPC299080
0.894 High Similarity NPC293852
0.894 High Similarity NPC62840
0.8938 High Similarity NPC473011
0.8933 High Similarity NPC159275
0.8933 High Similarity NPC241100
0.8924 High Similarity NPC271741
0.8924 High Similarity NPC324358
0.8924 High Similarity NPC322459
0.8924 High Similarity NPC318527
0.8924 High Similarity NPC208258
0.8924 High Similarity NPC268360
0.8924 High Similarity NPC323627
0.8924 High Similarity NPC287789
0.8917 High Similarity NPC148938
0.891 High Similarity NPC87708
0.891 High Similarity NPC154683
0.891 High Similarity NPC43345
0.891 High Similarity NPC40356
0.8903 High Similarity NPC472633
0.8903 High Similarity NPC307780
0.8903 High Similarity NPC309979
0.8903 High Similarity NPC227122
0.8896 High Similarity NPC161191
0.8896 High Similarity NPC266572
0.8896 High Similarity NPC475212
0.8896 High Similarity NPC6511
0.8896 High Similarity NPC189087
0.8896 High Similarity NPC300307
0.8896 High Similarity NPC244407
0.8896 High Similarity NPC321623
0.8889 High Similarity NPC109183
0.8889 High Similarity NPC473078
0.8889 High Similarity NPC320741
0.8889 High Similarity NPC477835
0.8889 High Similarity NPC470132
0.8889 High Similarity NPC228779
0.8889 High Similarity NPC470131
0.8889 High Similarity NPC474161
0.8889 High Similarity NPC470133
0.8889 High Similarity NPC476088
0.8889 High Similarity NPC171985
0.8889 High Similarity NPC470134
0.8882 High Similarity NPC11700
0.8882 High Similarity NPC219915
0.8882 High Similarity NPC189650
0.8874 High Similarity NPC110969
0.8874 High Similarity NPC282300
0.8867 High Similarity NPC220062
0.8867 High Similarity NPC18260
0.8867 High Similarity NPC96565
0.8867 High Similarity NPC78913
0.8867 High Similarity NPC55018

  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 NPC18699 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
0.9236 High Similarity NPD6959 Discontinued
0.8947 High Similarity NPD7410 Clinical (unspecified phase)
0.8944 High Similarity NPD7852 Clinical (unspecified phase)
0.8917 High Similarity NPD8443 Clinical (unspecified phase)
0.8854 High Similarity NPD7819 Suspended
0.8824 High Similarity NPD4378 Clinical (unspecified phase)
0.8742 High Similarity NPD7768 Phase 2
0.8636 High Similarity NPD7390 Discontinued
0.8608 High Similarity NPD7411 Suspended
0.85 High Similarity NPD2393 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD6232 Discontinued
0.8457 Intermediate Similarity NPD3749 Approved
0.8434 Intermediate Similarity NPD7473 Discontinued
0.8428 Intermediate Similarity NPD4380 Phase 2
0.8373 Intermediate Similarity NPD6166 Phase 2
0.8373 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8355 Intermediate Similarity NPD1510 Phase 2
0.8323 Intermediate Similarity NPD3750 Approved
0.8312 Intermediate Similarity NPD1549 Phase 2
0.8312 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD2796 Approved
0.828 Intermediate Similarity NPD1511 Approved
0.8272 Intermediate Similarity NPD2801 Approved
0.8232 Intermediate Similarity NPD7075 Discontinued
0.8225 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8212 Intermediate Similarity NPD1240 Approved
0.821 Intermediate Similarity NPD1934 Approved
0.8176 Intermediate Similarity NPD1512 Approved
0.8121 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8118 Intermediate Similarity NPD5844 Phase 1
0.8105 Intermediate Similarity NPD1607 Approved
0.8098 Intermediate Similarity NPD6801 Discontinued
0.8049 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD3226 Approved
0.8025 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD7054 Approved
0.8 Intermediate Similarity NPD2533 Approved
0.8 Intermediate Similarity NPD2532 Approved
0.8 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD2534 Approved
0.8 Intermediate Similarity NPD3748 Approved
0.8 Intermediate Similarity NPD3817 Phase 2
0.7965 Intermediate Similarity NPD7472 Approved
0.7965 Intermediate Similarity NPD7074 Phase 3
0.7952 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD3882 Suspended
0.7949 Intermediate Similarity NPD5405 Approved
0.7949 Intermediate Similarity NPD5404 Approved
0.7949 Intermediate Similarity NPD5406 Approved
0.7949 Intermediate Similarity NPD5408 Approved
0.7931 Intermediate Similarity NPD7808 Phase 3
0.7919 Intermediate Similarity NPD6797 Phase 2
0.7919 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD5494 Approved
0.7911 Intermediate Similarity NPD2800 Approved
0.7886 Intermediate Similarity NPD8312 Approved
0.7886 Intermediate Similarity NPD8313 Approved
0.7874 Intermediate Similarity NPD6559 Discontinued
0.7874 Intermediate Similarity NPD7251 Discontinued
0.7865 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD3818 Discontinued
0.7843 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD2935 Discontinued
0.7826 Intermediate Similarity NPD6799 Approved
0.7799 Intermediate Similarity NPD1243 Approved
0.7791 Intermediate Similarity NPD5403 Approved
0.7785 Intermediate Similarity NPD2344 Approved
0.7784 Intermediate Similarity NPD5402 Approved
0.7778 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD6599 Discontinued
0.7756 Intermediate Similarity NPD6651 Approved
0.775 Intermediate Similarity NPD7003 Approved
0.7727 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD1465 Phase 2
0.7722 Intermediate Similarity NPD6100 Approved
0.7722 Intermediate Similarity NPD6099 Approved
0.7712 Intermediate Similarity NPD4908 Phase 1
0.7697 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD920 Approved
0.7674 Intermediate Similarity NPD3926 Phase 2
0.7673 Intermediate Similarity NPD2346 Discontinued
0.7669 Intermediate Similarity NPD5401 Approved
0.7662 Intermediate Similarity NPD4625 Phase 3
0.7658 Intermediate Similarity NPD2799 Discontinued
0.7654 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD7177 Discontinued
0.7627 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7229 Phase 3
0.7614 Intermediate Similarity NPD5953 Discontinued
0.7613 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD1551 Phase 2
0.7593 Intermediate Similarity NPD2309 Approved
0.7561 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD919 Approved
0.7539 Intermediate Similarity NPD8151 Discontinued
0.7515 Intermediate Similarity NPD8455 Phase 2
0.7514 Intermediate Similarity NPD3787 Discontinued
0.7514 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2313 Discontinued
0.7483 Intermediate Similarity NPD1201 Approved
0.7473 Intermediate Similarity NPD4287 Approved
0.747 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD7199 Phase 2
0.7457 Intermediate Similarity NPD1247 Approved
0.7443 Intermediate Similarity NPD3751 Discontinued
0.7423 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7870 Phase 2
0.7421 Intermediate Similarity NPD7871 Phase 2
0.7414 Intermediate Similarity NPD5711 Approved
0.7414 Intermediate Similarity NPD5710 Approved
0.7405 Intermediate Similarity NPD943 Approved
0.7405 Intermediate Similarity NPD4363 Phase 3
0.7405 Intermediate Similarity NPD4360 Phase 2
0.7403 Intermediate Similarity NPD1470 Approved
0.7401 Intermediate Similarity NPD7286 Phase 2
0.7394 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6776 Approved
0.7394 Intermediate Similarity NPD6779 Approved
0.7394 Intermediate Similarity NPD6780 Approved
0.7394 Intermediate Similarity NPD6777 Approved
0.7394 Intermediate Similarity NPD6781 Approved
0.7394 Intermediate Similarity NPD6778 Approved
0.7394 Intermediate Similarity NPD6782 Approved
0.7389 Intermediate Similarity NPD3268 Approved
0.7381 Intermediate Similarity NPD7458 Discontinued
0.7371 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7783 Phase 2
0.7368 Intermediate Similarity NPD7698 Approved
0.7368 Intermediate Similarity NPD7696 Phase 3
0.7368 Intermediate Similarity NPD7697 Approved
0.7368 Intermediate Similarity NPD4288 Approved
0.7355 Intermediate Similarity NPD2798 Approved
0.7317 Intermediate Similarity NPD4628 Phase 3
0.7305 Intermediate Similarity NPD6273 Approved
0.729 Intermediate Similarity NPD1203 Approved
0.729 Intermediate Similarity NPD2797 Approved
0.7278 Intermediate Similarity NPD3764 Approved
0.7277 Intermediate Similarity NPD7435 Discontinued
0.7273 Intermediate Similarity NPD4361 Phase 2
0.7273 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD8150 Discontinued
0.7261 Intermediate Similarity NPD6832 Phase 2
0.7255 Intermediate Similarity NPD1610 Phase 2
0.725 Intermediate Similarity NPD5124 Phase 1
0.725 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD3225 Approved
0.7222 Intermediate Similarity NPD7033 Discontinued
0.7219 Intermediate Similarity NPD1548 Phase 1
0.7216 Intermediate Similarity NPD7701 Phase 2
0.7208 Intermediate Similarity NPD1608 Approved
0.7186 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD1651 Approved
0.7151 Intermediate Similarity NPD37 Approved
0.7143 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD422 Phase 1
0.7143 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6234 Discontinued
0.7143 Intermediate Similarity NPD7874 Approved
0.7135 Intermediate Similarity NPD6823 Phase 2
0.7134 Intermediate Similarity NPD1471 Phase 3
0.7128 Intermediate Similarity NPD6535 Approved
0.7128 Intermediate Similarity NPD6534 Approved
0.7126 Intermediate Similarity NPD4967 Phase 2
0.7126 Intermediate Similarity NPD4966 Approved
0.7126 Intermediate Similarity NPD4965 Approved
0.7117 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD4308 Phase 3
0.7115 Intermediate Similarity NPD1283 Approved
0.7107 Intermediate Similarity NPD7801 Approved
0.7105 Intermediate Similarity NPD7700 Phase 2
0.7105 Intermediate Similarity NPD7699 Phase 2
0.7097 Intermediate Similarity NPD9717 Approved
0.7087 Intermediate Similarity NPD7654 Discontinued
0.7081 Intermediate Similarity NPD4060 Phase 1
0.707 Intermediate Similarity NPD3266 Approved
0.707 Intermediate Similarity NPD3267 Approved
0.7069 Intermediate Similarity NPD2296 Approved
0.7056 Intermediate Similarity NPD7228 Approved
0.7056 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4749 Approved
0.7048 Intermediate Similarity NPD2654 Approved
0.7044 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7447 Phase 1
0.7039 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD17 Approved
0.6994 Remote Similarity NPD7615 Clinical (unspecified phase)
0.699 Remote Similarity NPD7584 Approved
0.6989 Remote Similarity NPD8434 Phase 2
0.6989 Remote Similarity NPD6971 Discontinued
0.6987 Remote Similarity NPD3972 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