Structure

Physi-Chem Properties

Molecular Weight:  756.34
Volume:  785.852
LogP:  8.727
LogD:  3.514
LogS:  -4.164
# Rotatable Bonds:  5
TPSA:  163.9
# H-Bond Aceptor:  10
# H-Bond Donor:  8
# Rings:  8
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.085
Synthetic Accessibility Score:  4.957
Fsp3:  0.304
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.304
MDCK Permeability:  9.042526471603196e-06
Pgp-inhibitor:  0.926
Pgp-substrate:  0.926
Human Intestinal Absorption (HIA):  0.746
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  91.04498291015625%
Volume Distribution (VD):  0.438
Pgp-substrate:  9.640522003173828%

ADMET: Metabolism

CYP1A2-inhibitor:  0.519
CYP1A2-substrate:  0.894
CYP2C19-inhibitor:  0.277
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.123
CYP2C9-substrate:  0.179
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.595
CYP3A4-inhibitor:  0.012
CYP3A4-substrate:  0.144

ADMET: Excretion

Clearance (CL):  2.377
Half-life (T1/2):  0.009

ADMET: Toxicity

hERG Blockers:  0.074
Human Hepatotoxicity (H-HT):  0.969
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.173
Rat Oral Acute Toxicity:  0.085
Maximum Recommended Daily Dose:  1.0
Skin Sensitization:  0.905
Carcinogencity:  0.011
Eye Corrosion:  0.003
Eye Irritation:  0.029
Respiratory Toxicity:  0.766

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

  Natural Product: NPC119068

Natural Product ID:  NPC119068
Common Name*:   (1S,3S)-5-[3-[4-[(1S,3S)-6,8-Dihydroxy-1,3-Dimethyl-1,2,3,4-Tetrahydroisoquinolin-5-Yl]-1-Hydroxy-8-Methoxy-6-Methylnaphthalen-2-Yl]-4-Hydroxy-5-Methoxy-7-Methylnaphthalen-1-Yl]-1,3-Dimethyl-1,2,3,4-Tetrahydroisoquinoline-6,8-Diol
IUPAC Name:   (1S,3S)-5-[3-[4-[(1S,3S)-6,8-dihydroxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-1-hydroxy-8-methoxy-6-methylnaphthalen-2-yl]-4-hydroxy-5-methoxy-7-methylnaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,8-diol
Synonyms:  
Standard InCHIKey:  GMLBVLXDRNJFGR-ZJZGAYNASA-N
Standard InCHI:  InChI=1S/C46H48N2O8/c1-19-9-25-27(41-31-13-21(3)47-23(5)39(31)33(49)17-35(41)51)15-29(45(53)43(25)37(11-19)55-7)30-16-28(26-10-20(2)12-38(56-8)44(26)46(30)54)42-32-14-22(4)48-24(6)40(32)34(50)18-36(42)52/h9-12,15-18,21-24,47-54H,13-14H2,1-8H3/t21-,22-,23-,24-/m0/s1
SMILES:  Cc1cc2c(cc(c3cc(c4cc(C)cc(c4c3O)OC)c3c4C[C@H](C)N[C@@H](C)c4c(cc3O)O)c(c2c(c1)OC)O)c1c2C[C@H](C)N[C@@H](C)c2c(cc1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL325222
PubChem CID:   453654
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0002195] Naphthylisoquinolines

*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
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. Cameroon n.a. PMID[11430019]
NPO28537 Ancistrocladus abbreviatus Species Ancistrocladaceae Eukaryota n.a. aerial part n.a. PMID[1766007]
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO28537 Ancistrocladus abbreviatus Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. PMID[31642313]
NPO28537 Ancistrocladus abbreviatus Species Ancistrocladaceae Eukaryota Roots n.a. n.a. PMID[32125158]
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. PMID[9249970]
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. PMID[9873424]
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28537 Ancistrocladus abbreviatus Species Ancistrocladaceae 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
NPT315 Cell Line CEM-SS Homo sapiens EC50 = 20000.0 nM PMID[447737]
NPT315 Cell Line CEM-SS Homo sapiens IC50 = 200000.0 nM PMID[447737]
NPT315 Cell Line CEM-SS Homo sapiens EC50 = 20000.0 nM PMID[447738]
NPT315 Cell Line CEM-SS Homo sapiens IC50 = 200000.0 nM PMID[447738]

☑ 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 NPC119068 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 NPC40496
0.9939 High Similarity NPC230276
0.9939 High Similarity NPC257269
0.9302 High Similarity NPC259350
0.9302 High Similarity NPC223236
0.9264 High Similarity NPC209377
0.9249 High Similarity NPC476565
0.9207 High Similarity NPC56887
0.9207 High Similarity NPC193853
0.9207 High Similarity NPC223077
0.9091 High Similarity NPC195392
0.8977 High Similarity NPC256124
0.8957 High Similarity NPC79328
0.8909 High Similarity NPC79402
0.8909 High Similarity NPC80759
0.8902 High Similarity NPC221864
0.8902 High Similarity NPC7393
0.8896 High Similarity NPC29647
0.8848 High Similarity NPC119649
0.8848 High Similarity NPC271388
0.8848 High Similarity NPC205255
0.8848 High Similarity NPC230956
0.8848 High Similarity NPC235143
0.8743 High Similarity NPC95426
0.8743 High Similarity NPC16357
0.8743 High Similarity NPC302245
0.8701 High Similarity NPC11296
0.8701 High Similarity NPC82457
0.8701 High Similarity NPC48490
0.8701 High Similarity NPC175890
0.8701 High Similarity NPC274661
0.8693 High Similarity NPC65312
0.8693 High Similarity NPC139783
0.8652 High Similarity NPC60295
0.8652 High Similarity NPC191132
0.8644 High Similarity NPC275680
0.8644 High Similarity NPC22115
0.8606 High Similarity NPC123323
0.8556 High Similarity NPC473589
0.8556 High Similarity NPC478091
0.8556 High Similarity NPC478092
0.8556 High Similarity NPC30182
0.8514 High Similarity NPC243454
0.8514 High Similarity NPC475479
0.85 High Similarity NPC478093
0.8466 Intermediate Similarity NPC239584
0.8418 Intermediate Similarity NPC8836
0.8418 Intermediate Similarity NPC15414
0.8418 Intermediate Similarity NPC42663
0.8418 Intermediate Similarity NPC328155
0.8418 Intermediate Similarity NPC271013
0.8418 Intermediate Similarity NPC285931
0.8418 Intermediate Similarity NPC251735
0.8418 Intermediate Similarity NPC7715
0.8418 Intermediate Similarity NPC104196
0.8418 Intermediate Similarity NPC279228
0.8418 Intermediate Similarity NPC54654
0.8418 Intermediate Similarity NPC182052
0.8418 Intermediate Similarity NPC239824
0.8418 Intermediate Similarity NPC258657
0.8418 Intermediate Similarity NPC217748
0.8418 Intermediate Similarity NPC290582
0.8418 Intermediate Similarity NPC229373
0.8418 Intermediate Similarity NPC223690
0.8418 Intermediate Similarity NPC49075
0.8418 Intermediate Similarity NPC290005
0.8418 Intermediate Similarity NPC181796
0.8418 Intermediate Similarity NPC90998
0.8418 Intermediate Similarity NPC311973
0.8418 Intermediate Similarity NPC30779
0.8418 Intermediate Similarity NPC185639
0.8418 Intermediate Similarity NPC222661
0.8409 Intermediate Similarity NPC474507
0.8389 Intermediate Similarity NPC206900
0.838 Intermediate Similarity NPC116465
0.838 Intermediate Similarity NPC212237
0.838 Intermediate Similarity NPC47077
0.838 Intermediate Similarity NPC14507
0.8371 Intermediate Similarity NPC274716
0.8371 Intermediate Similarity NPC167116
0.8371 Intermediate Similarity NPC302275
0.8371 Intermediate Similarity NPC254441
0.8362 Intermediate Similarity NPC286119
0.8295 Intermediate Similarity NPC148709
0.8295 Intermediate Similarity NPC476577
0.8295 Intermediate Similarity NPC173416
0.8278 Intermediate Similarity NPC57036
0.8266 Intermediate Similarity NPC204947
0.8229 Intermediate Similarity NPC317439
0.8229 Intermediate Similarity NPC76682
0.8229 Intermediate Similarity NPC108434
0.8229 Intermediate Similarity NPC276890
0.8229 Intermediate Similarity NPC198498
0.8229 Intermediate Similarity NPC63646
0.8229 Intermediate Similarity NPC115284
0.8229 Intermediate Similarity NPC317145
0.8229 Intermediate Similarity NPC10908
0.8229 Intermediate Similarity NPC227060
0.8229 Intermediate Similarity NPC475215
0.8192 Intermediate Similarity NPC293093
0.8187 Intermediate Similarity NPC281581
0.8182 Intermediate Similarity NPC129518
0.8182 Intermediate Similarity NPC251580
0.8182 Intermediate Similarity NPC66341
0.8182 Intermediate Similarity NPC41376
0.8182 Intermediate Similarity NPC12424
0.8182 Intermediate Similarity NPC192135
0.8182 Intermediate Similarity NPC477020
0.8171 Intermediate Similarity NPC26240
0.8171 Intermediate Similarity NPC69712
0.8171 Intermediate Similarity NPC477562
0.815 Intermediate Similarity NPC24465
0.8132 Intermediate Similarity NPC186546
0.8132 Intermediate Similarity NPC476576
0.8125 Intermediate Similarity NPC239775
0.8103 Intermediate Similarity NPC264850
0.8103 Intermediate Similarity NPC13916
0.8098 Intermediate Similarity NPC24260
0.8095 Intermediate Similarity NPC254581
0.8068 Intermediate Similarity NPC109925
0.8 Intermediate Similarity NPC470879
0.8 Intermediate Similarity NPC35627
0.8 Intermediate Similarity NPC476573
0.8 Intermediate Similarity NPC81247
0.8 Intermediate Similarity NPC258695
0.7989 Intermediate Similarity NPC475393
0.7968 Intermediate Similarity NPC234318
0.7966 Intermediate Similarity NPC118274
0.7966 Intermediate Similarity NPC168753
0.7956 Intermediate Similarity NPC474506
0.7956 Intermediate Similarity NPC32413
0.7943 Intermediate Similarity NPC4138
0.7943 Intermediate Similarity NPC121275
0.7943 Intermediate Similarity NPC284183
0.7931 Intermediate Similarity NPC60186
0.7927 Intermediate Similarity NPC273623
0.7912 Intermediate Similarity NPC73492
0.7912 Intermediate Similarity NPC299990
0.7898 Intermediate Similarity NPC250846
0.7898 Intermediate Similarity NPC240841
0.7898 Intermediate Similarity NPC256012
0.7898 Intermediate Similarity NPC268503
0.7898 Intermediate Similarity NPC317272
0.7898 Intermediate Similarity NPC42549
0.7886 Intermediate Similarity NPC1229
0.7886 Intermediate Similarity NPC324144
0.7869 Intermediate Similarity NPC135772
0.7861 Intermediate Similarity NPC85381
0.7861 Intermediate Similarity NPC195766
0.7861 Intermediate Similarity NPC206736
0.7857 Intermediate Similarity NPC477561
0.7857 Intermediate Similarity NPC155442
0.7857 Intermediate Similarity NPC476574
0.7857 Intermediate Similarity NPC312918
0.7853 Intermediate Similarity NPC474931
0.7853 Intermediate Similarity NPC145832
0.7853 Intermediate Similarity NPC306555
0.7853 Intermediate Similarity NPC12053
0.7853 Intermediate Similarity NPC81218
0.7853 Intermediate Similarity NPC158376
0.7853 Intermediate Similarity NPC117188
0.7853 Intermediate Similarity NPC205421
0.7849 Intermediate Similarity NPC318805
0.7849 Intermediate Similarity NPC41122
0.7845 Intermediate Similarity NPC23219
0.7842 Intermediate Similarity NPC475654
0.7841 Intermediate Similarity NPC13504
0.7841 Intermediate Similarity NPC477563
0.7841 Intermediate Similarity NPC306843
0.7841 Intermediate Similarity NPC196447
0.7841 Intermediate Similarity NPC253043
0.7841 Intermediate Similarity NPC136508
0.7841 Intermediate Similarity NPC96603
0.7841 Intermediate Similarity NPC78222
0.7841 Intermediate Similarity NPC212794
0.7836 Intermediate Similarity NPC114124
0.7807 Intermediate Similarity NPC117717
0.7805 Intermediate Similarity NPC71465
0.7805 Intermediate Similarity NPC472646
0.7803 Intermediate Similarity NPC203784
0.7803 Intermediate Similarity NPC170503
0.7803 Intermediate Similarity NPC126519
0.7791 Intermediate Similarity NPC2295
0.7791 Intermediate Similarity NPC477564
0.779 Intermediate Similarity NPC112575
0.7765 Intermediate Similarity NPC207824
0.7765 Intermediate Similarity NPC92541
0.7765 Intermediate Similarity NPC60538
0.7754 Intermediate Similarity NPC475754
0.7746 Intermediate Similarity NPC295691
0.7746 Intermediate Similarity NPC278799
0.7746 Intermediate Similarity NPC127674
0.7746 Intermediate Similarity NPC39701
0.7746 Intermediate Similarity NPC187022
0.7746 Intermediate Similarity NPC189266
0.7746 Intermediate Similarity NPC184026
0.7746 Intermediate Similarity NPC5238
0.7746 Intermediate Similarity NPC2413
0.7746 Intermediate Similarity NPC204828
0.7746 Intermediate Similarity NPC193949

  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 NPC119068 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
1.0 High Similarity NPD8453 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD8054 Approved
0.8418 Intermediate Similarity NPD8053 Approved
0.8229 Intermediate Similarity NPD8252 Approved
0.8229 Intermediate Similarity NPD8099 Discontinued
0.8229 Intermediate Similarity NPD8251 Approved
0.8182 Intermediate Similarity NPD8156 Discontinued
0.7904 Intermediate Similarity NPD7598 Phase 2
0.7816 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7298 Approved
0.7637 Intermediate Similarity NPD7479 Phase 2
0.7605 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD4584 Approved
0.7529 Intermediate Similarity NPD3845 Phase 1
0.7486 Intermediate Similarity NPD42 Phase 2
0.7486 Intermediate Similarity NPD6042 Phase 2
0.7423 Intermediate Similarity NPD8095 Phase 1
0.7416 Intermediate Similarity NPD6788 Approved
0.7341 Intermediate Similarity NPD7447 Phase 1
0.7303 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD6090 Discontinued
0.7283 Intermediate Similarity NPD2420 Approved
0.7283 Intermediate Similarity NPD2421 Approved
0.7243 Intermediate Similarity NPD7493 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD1424 Approved
0.7238 Intermediate Similarity NPD5709 Phase 3
0.7225 Intermediate Similarity NPD7906 Approved
0.7225 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD2568 Approved
0.7198 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD4666 Phase 3
0.7193 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD7212 Phase 2
0.7184 Intermediate Similarity NPD7213 Phase 3
0.716 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD4773 Phase 2
0.7095 Intermediate Similarity NPD4772 Phase 2
0.7088 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD7833 Phase 2
0.7088 Intermediate Similarity NPD7831 Phase 2
0.7086 Intermediate Similarity NPD3124 Discontinued
0.7085 Intermediate Similarity NPD8153 Approved
0.7085 Intermediate Similarity NPD8152 Approved
0.7081 Intermediate Similarity NPD8051 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD6107 Approved
0.7062 Intermediate Similarity NPD6031 Approved
0.7062 Intermediate Similarity NPD6030 Approved
0.7059 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD4474 Approved
0.7024 Intermediate Similarity NPD4475 Approved
0.7 Intermediate Similarity NPD7438 Suspended
0.6995 Remote Similarity NPD4055 Discovery
0.6995 Remote Similarity NPD6973 Clinical (unspecified phase)
0.6994 Remote Similarity NPD4257 Approved
0.6994 Remote Similarity NPD4256 Phase 2
0.699 Remote Similarity NPD7827 Phase 1
0.6985 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6983 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6982 Remote Similarity NPD2238 Phase 2
0.6974 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6971 Remote Similarity NPD8131 Suspended
0.697 Remote Similarity NPD6284 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4727 Phase 1
0.6954 Remote Similarity NPD3060 Approved
0.6949 Remote Similarity NPD3157 Approved
0.6949 Remote Similarity NPD3158 Phase 1
0.6935 Remote Similarity NPD6747 Phase 1
0.6927 Remote Similarity NPD7313 Approved
0.6927 Remote Similarity NPD7311 Approved
0.6927 Remote Similarity NPD7310 Approved
0.6927 Remote Similarity NPD7312 Approved
0.6923 Remote Similarity NPD6407 Approved
0.6923 Remote Similarity NPD6405 Approved
0.6923 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4585 Approved
0.6919 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4625 Phase 3
0.6893 Remote Similarity NPD6087 Phase 1
0.6891 Remote Similarity NPD7309 Approved
0.6882 Remote Similarity NPD6959 Discontinued
0.6882 Remote Similarity NPD3109 Approved
0.6882 Remote Similarity NPD3110 Approved
0.6875 Remote Similarity NPD5160 Discontinued
0.6872 Remote Similarity NPD7693 Approved
0.6864 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6862 Remote Similarity NPD27 Approved
0.6862 Remote Similarity NPD2489 Approved
0.6862 Remote Similarity NPD2898 Approved
0.6859 Remote Similarity NPD6297 Approved
0.6854 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6845 Remote Similarity NPD4010 Discontinued
0.6845 Remote Similarity NPD6071 Discontinued
0.6845 Remote Similarity NPD3051 Approved
0.6839 Remote Similarity NPD4577 Approved
0.6839 Remote Similarity NPD4578 Approved
0.6831 Remote Similarity NPD2978 Approved
0.6831 Remote Similarity NPD2977 Approved
0.6826 Remote Similarity NPD602 Approved
0.6826 Remote Similarity NPD599 Approved
0.6821 Remote Similarity NPD1753 Discontinued
0.6821 Remote Similarity NPD4663 Approved
0.6818 Remote Similarity NPD6748 Discontinued
0.6816 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6814 Remote Similarity NPD7870 Phase 2
0.6814 Remote Similarity NPD7871 Phase 2
0.6813 Remote Similarity NPD6072 Discontinued
0.6811 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6809 Remote Similarity NPD2970 Approved
0.6809 Remote Similarity NPD2969 Approved
0.6804 Remote Similarity NPD6853 Approved
0.6804 Remote Similarity NPD6851 Approved
0.6802 Remote Similarity NPD3054 Approved
0.6802 Remote Similarity NPD3052 Approved
0.68 Remote Similarity NPD7037 Approved
0.6796 Remote Similarity NPD4005 Discontinued
0.678 Remote Similarity NPD2677 Approved
0.678 Remote Similarity NPD5307 Clinical (unspecified phase)
0.678 Remote Similarity NPD5241 Discontinued
0.6779 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6779 Remote Similarity NPD7783 Phase 2
0.6778 Remote Similarity NPD3640 Phase 3
0.6778 Remote Similarity NPD3639 Approved
0.6778 Remote Similarity NPD3641 Approved
0.6774 Remote Similarity NPD7400 Phase 3
0.6774 Remote Similarity NPD7654 Discontinued
0.6768 Remote Similarity NPD2688 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7697 Approved
0.6765 Remote Similarity NPD7696 Phase 3
0.6765 Remote Similarity NPD7698 Approved
0.6763 Remote Similarity NPD3553 Approved
0.6763 Remote Similarity NPD3554 Approved
0.6763 Remote Similarity NPD3555 Approved
0.6763 Remote Similarity NPD3552 Approved
0.6761 Remote Similarity NPD2460 Phase 3
0.6761 Remote Similarity NPD2458 Approved
0.6761 Remote Similarity NPD2459 Approved
0.676 Remote Similarity NPD2874 Phase 2
0.6757 Remote Similarity NPD7773 Phase 2
0.6755 Remote Similarity NPD4166 Phase 2
0.6753 Remote Similarity NPD6146 Clinical (unspecified phase)
0.6746 Remote Similarity NPD4908 Phase 1
0.6743 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6742 Remote Similarity NPD7124 Phase 2
0.6742 Remote Similarity NPD6667 Approved
0.6742 Remote Similarity NPD6666 Approved
0.6742 Remote Similarity NPD3122 Phase 3
0.6739 Remote Similarity NPD6064 Phase 1
0.6738 Remote Similarity NPD6746 Phase 2
0.6727 Remote Similarity NPD7922 Phase 1
0.6726 Remote Similarity NPD858 Approved
0.6726 Remote Similarity NPD859 Approved
0.6724 Remote Similarity NPD2156 Approved
0.6724 Remote Similarity NPD2155 Approved
0.6724 Remote Similarity NPD2154 Approved
0.6723 Remote Similarity NPD7466 Approved
0.672 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6716 Remote Similarity NPD6823 Phase 2
0.6715 Remote Similarity NPD7701 Phase 2
0.6706 Remote Similarity NPD5155 Approved
0.6706 Remote Similarity NPD5156 Approved
0.6705 Remote Similarity NPD4097 Suspended
0.6703 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6703 Remote Similarity NPD4017 Approved
0.6702 Remote Similarity NPD7802 Discontinued
0.6702 Remote Similarity NPD7177 Discontinued
0.6701 Remote Similarity NPD7549 Discontinued
0.6687 Remote Similarity NPD2232 Approved
0.6687 Remote Similarity NPD2233 Approved
0.6687 Remote Similarity NPD2230 Approved
0.6685 Remote Similarity NPD3692 Discontinued
0.6684 Remote Similarity NPD6607 Clinical (unspecified phase)
0.6684 Remote Similarity NPD6996 Clinical (unspecified phase)
0.6683 Remote Similarity NPD8151 Discontinued
0.6667 Remote Similarity NPD7020 Approved
0.6667 Remote Similarity NPD7861 Discontinued
0.6667 Remote Similarity NPD2200 Suspended
0.6667 Remote Similarity NPD5895 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7019 Approved
0.6667 Remote Similarity NPD6020 Phase 2
0.6652 Remote Similarity NPD6723 Discontinued
0.6649 Remote Similarity NPD6037 Discontinued
0.6647 Remote Similarity NPD3594 Approved
0.6647 Remote Similarity NPD2606 Approved
0.6647 Remote Similarity NPD596 Approved
0.6647 Remote Similarity NPD600 Approved
0.6647 Remote Similarity NPD2605 Approved
0.6647 Remote Similarity NPD1669 Approved
0.6647 Remote Similarity NPD3595 Approved
0.6636 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6633 Remote Similarity NPD7090 Clinical (unspecified phase)
0.663 Remote Similarity NPD2676 Approved
0.663 Remote Similarity NPD5261 Clinical (unspecified phase)
0.663 Remote Similarity NPD2675 Approved
0.6629 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6629 Remote Similarity NPD7066 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