Structure

Physi-Chem Properties

Molecular Weight:  698.32
Volume:  709.969
LogP:  5.078
LogD:  3.253
LogS:  -3.892
# Rotatable Bonds:  10
TPSA:  111.55
# H-Bond Aceptor:  11
# H-Bond Donor:  2
# Rings:  7
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.19
Synthetic Accessibility Score:  4.201
Fsp3:  0.4
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.468
MDCK Permeability:  2.8739606932504103e-05
Pgp-inhibitor:  0.99
Pgp-substrate:  0.863
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.116

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.055
Plasma Protein Binding (PPB):  54.82004928588867%
Volume Distribution (VD):  1.248
Pgp-substrate:  58.187339782714844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.992
CYP2C19-inhibitor:  0.038
CYP2C19-substrate:  0.969
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.782
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.936
CYP3A4-inhibitor:  0.06
CYP3A4-substrate:  0.963

ADMET: Excretion

Clearance (CL):  9.518
Half-life (T1/2):  0.204

ADMET: Toxicity

hERG Blockers:  0.955
Human Hepatotoxicity (H-HT):  0.037
Drug-inuced Liver Injury (DILI):  0.386
AMES Toxicity:  0.056
Rat Oral Acute Toxicity:  0.841
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.909
Carcinogencity:  0.013
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.637

Download Data

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

  Natural Product: NPC30182

Natural Product ID:  NPC30182
Common Name*:   Thalifasine
IUPAC Name:   (6aS)-8-[4-[[(1S)-5-hydroxy-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]phenoxy]-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-3-ol
Synonyms:   Thalifasine
Standard InCHIKey:  JKZGCTOQBIITDP-VMPREFPWSA-N
Standard InCHI:  InChI=1S/C40H46N2O9/c1-41-15-13-23-25(19-30(45-3)37(47-5)34(23)43)28(41)17-21-9-11-22(12-10-21)51-36-27-18-29-32-24(14-16-42(29)2)35(44)40(50-8)39(49-7)33(32)26(27)20-31(46-4)38(36)48-6/h9-12,19-20,28-29,43-44H,13-18H2,1-8H3/t28-,29-/m0/s1
SMILES:  COc1c(OC)cc2c(c1Oc1ccc(cc1)C[C@@H]1N(C)CCc3c1cc(OC)c(c3O)OC)C[C@H]1c3c2c(OC)c(c(c3CCN1C)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL510732
PubChem CID:   10372546
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO21435 Thalictrum faberi Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[19299148]
NPO21435 Thalictrum faberi Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[7528786]
NPO21435 Thalictrum faberi Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21435 Thalictrum faberi Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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
NPT453 Cell Line HT-1080 Homo sapiens ED50 = 1.3 ug ml-1 PMID[470997]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 2.0 ug ml-1 PMID[470997]
NPT1851 Cell Line Col2 Homo sapiens ED50 = 2.1 ug ml-1 PMID[470997]
NPT91 Cell Line KB Homo sapiens ED50 = 4.6 ug ml-1 PMID[470997]
NPT168 Cell Line P388 Mus musculus ED50 = 1.2 ug ml-1 PMID[470997]
NPT762 Cell Line A-431 Homo sapiens ED50 = 8.2 ug ml-1 PMID[470997]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 3.3 ug ml-1 PMID[470997]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 1.2 ug ml-1 PMID[470997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 2.4 ug ml-1 PMID[470997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 5.7 ug ml-1 PMID[470997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 1.6 ug ml-1 PMID[470997]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 2.2 ug ml-1 PMID[470997]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 238.0 ng/ml PMID[470997]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 49.3 ng/ml PMID[470997]
NPT2 Others Unspecified Selectivity Index = 19.0 n.a. PMID[470997]
NPT2 Others Unspecified Selectivity Index = 93.0 n.a. PMID[470997]

☑ 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 NPC30182 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 NPC478092
1.0 High Similarity NPC478091
1.0 High Similarity NPC473589
0.9942 High Similarity NPC478093
0.9593 High Similarity NPC302275
0.954 High Similarity NPC275680
0.954 High Similarity NPC22115
0.9535 High Similarity NPC30779
0.9477 High Similarity NPC286119
0.9425 High Similarity NPC16357
0.9425 High Similarity NPC95426
0.9425 High Similarity NPC302245
0.9422 High Similarity NPC15414
0.9422 High Similarity NPC290005
0.9422 High Similarity NPC222661
0.9422 High Similarity NPC42663
0.9422 High Similarity NPC104196
0.9422 High Similarity NPC90998
0.9422 High Similarity NPC290582
0.9422 High Similarity NPC49075
0.9422 High Similarity NPC217748
0.9422 High Similarity NPC182052
0.9422 High Similarity NPC311973
0.9422 High Similarity NPC271013
0.9422 High Similarity NPC8836
0.9422 High Similarity NPC7715
0.9422 High Similarity NPC181796
0.9422 High Similarity NPC328155
0.9422 High Similarity NPC279228
0.9422 High Similarity NPC251735
0.9422 High Similarity NPC239824
0.9422 High Similarity NPC229373
0.9422 High Similarity NPC223690
0.9422 High Similarity NPC185639
0.9422 High Similarity NPC54654
0.9422 High Similarity NPC258657
0.9422 High Similarity NPC285931
0.9375 High Similarity NPC206900
0.9371 High Similarity NPC47077
0.9371 High Similarity NPC65312
0.9371 High Similarity NPC139783
0.9371 High Similarity NPC14507
0.9368 High Similarity NPC254441
0.9368 High Similarity NPC274716
0.9368 High Similarity NPC167116
0.9261 High Similarity NPC212237
0.9261 High Similarity NPC116465
0.9157 High Similarity NPC175890
0.9157 High Similarity NPC82457
0.9157 High Similarity NPC11296
0.9157 High Similarity NPC274661
0.9157 High Similarity NPC48490
0.9128 High Similarity NPC239775
0.9111 High Similarity NPC256124
0.9106 High Similarity NPC191132
0.9106 High Similarity NPC60295
0.907 High Similarity NPC168753
0.907 High Similarity NPC118274
0.9056 High Similarity NPC24260
0.9017 High Similarity NPC76682
0.9017 High Similarity NPC317145
0.9017 High Similarity NPC276890
0.9017 High Similarity NPC198498
0.9017 High Similarity NPC317439
0.9017 High Similarity NPC10908
0.9017 High Similarity NPC63646
0.9017 High Similarity NPC115284
0.9017 High Similarity NPC227060
0.8966 High Similarity NPC251580
0.8966 High Similarity NPC41376
0.8966 High Similarity NPC129518
0.8966 High Similarity NPC12424
0.8895 High Similarity NPC250846
0.8895 High Similarity NPC42549
0.8895 High Similarity NPC318805
0.8895 High Similarity NPC240841
0.8895 High Similarity NPC256012
0.8895 High Similarity NPC268503
0.8895 High Similarity NPC41122
0.8895 High Similarity NPC317272
0.887 High Similarity NPC474507
0.8864 High Similarity NPC293093
0.8844 High Similarity NPC306555
0.8844 High Similarity NPC145832
0.8844 High Similarity NPC81218
0.8844 High Similarity NPC158376
0.8844 High Similarity NPC117188
0.8844 High Similarity NPC205421
0.8844 High Similarity NPC12053
0.8844 High Similarity NPC474931
0.8837 High Similarity NPC477563
0.8837 High Similarity NPC96603
0.8837 High Similarity NPC212794
0.8837 High Similarity NPC13504
0.8837 High Similarity NPC136508
0.8837 High Similarity NPC306843
0.8837 High Similarity NPC253043
0.8837 High Similarity NPC196447
0.8837 High Similarity NPC78222
0.8804 High Similarity NPC234318
0.8798 High Similarity NPC85381
0.8786 High Similarity NPC264850
0.8786 High Similarity NPC13916
0.8779 High Similarity NPC324144
0.8764 High Similarity NPC243454
0.8764 High Similarity NPC475479
0.8763 High Similarity NPC475654
0.8757 High Similarity NPC173416
0.8757 High Similarity NPC476577
0.8757 High Similarity NPC148709
0.8728 High Similarity NPC24465
0.8723 High Similarity NPC254581
0.8715 High Similarity NPC239584
0.8686 High Similarity NPC83198
0.8686 High Similarity NPC204908
0.8671 High Similarity NPC1229
0.8667 High Similarity NPC73492
0.8667 High Similarity NPC299990
0.8663 High Similarity NPC27410
0.8663 High Similarity NPC166014
0.8611 High Similarity NPC257269
0.8611 High Similarity NPC230276
0.8588 High Similarity NPC475215
0.8588 High Similarity NPC108434
0.8556 High Similarity NPC119068
0.8556 High Similarity NPC40496
0.8539 High Similarity NPC190783
0.8539 High Similarity NPC192135
0.8539 High Similarity NPC66341
0.8539 High Similarity NPC232386
0.8539 High Similarity NPC152680
0.8539 High Similarity NPC477020
0.8533 High Similarity NPC82763
0.8531 High Similarity NPC69712
0.8531 High Similarity NPC477562
0.8531 High Similarity NPC26240
0.8508 High Similarity NPC195538
0.8506 High Similarity NPC60186
0.85 High Similarity NPC320223
0.85 High Similarity NPC114364
0.8492 Intermediate Similarity NPC128560
0.8492 Intermediate Similarity NPC199465
0.8492 Intermediate Similarity NPC229166
0.8488 Intermediate Similarity NPC247639
0.8488 Intermediate Similarity NPC25084
0.8478 Intermediate Similarity NPC476576
0.8478 Intermediate Similarity NPC186546
0.847 Intermediate Similarity NPC249996
0.8462 Intermediate Similarity NPC476202
0.8448 Intermediate Similarity NPC205255
0.8448 Intermediate Similarity NPC271388
0.8448 Intermediate Similarity NPC235143
0.8448 Intermediate Similarity NPC119649
0.8448 Intermediate Similarity NPC230956
0.8439 Intermediate Similarity NPC476572
0.8434 Intermediate Similarity NPC82056
0.8432 Intermediate Similarity NPC281581
0.843 Intermediate Similarity NPC325871
0.843 Intermediate Similarity NPC99659
0.8418 Intermediate Similarity NPC204947
0.84 Intermediate Similarity NPC79402
0.84 Intermediate Similarity NPC80759
0.8391 Intermediate Similarity NPC221864
0.8387 Intermediate Similarity NPC473716
0.8387 Intermediate Similarity NPC475597
0.838 Intermediate Similarity NPC149090
0.838 Intermediate Similarity NPC19520
0.8362 Intermediate Similarity NPC476573
0.8362 Intermediate Similarity NPC35627
0.8362 Intermediate Similarity NPC81247
0.8324 Intermediate Similarity NPC276588
0.8324 Intermediate Similarity NPC193949
0.8324 Intermediate Similarity NPC207757
0.8324 Intermediate Similarity NPC5238
0.8324 Intermediate Similarity NPC214116
0.8324 Intermediate Similarity NPC469817
0.8324 Intermediate Similarity NPC39701
0.8324 Intermediate Similarity NPC172765
0.8324 Intermediate Similarity NPC110416
0.8324 Intermediate Similarity NPC189266
0.8324 Intermediate Similarity NPC54379
0.8324 Intermediate Similarity NPC2413
0.8324 Intermediate Similarity NPC204828
0.8324 Intermediate Similarity NPC278799
0.8324 Intermediate Similarity NPC57036
0.8324 Intermediate Similarity NPC127674
0.8324 Intermediate Similarity NPC184026
0.8324 Intermediate Similarity NPC249797
0.8324 Intermediate Similarity NPC295691
0.8289 Intermediate Similarity NPC475754
0.8278 Intermediate Similarity NPC231371
0.8261 Intermediate Similarity NPC116284
0.8256 Intermediate Similarity NPC81733
0.8256 Intermediate Similarity NPC326316
0.8251 Intermediate Similarity NPC32154
0.8249 Intermediate Similarity NPC475393
0.8241 Intermediate Similarity NPC38964
0.8218 Intermediate Similarity NPC123323
0.8216 Intermediate Similarity NPC135772
0.8212 Intermediate Similarity NPC298979

  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 NPC30182 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
0.9422 High Similarity NPD8053 Approved
0.9422 High Similarity NPD8054 Approved
0.9017 High Similarity NPD8251 Approved
0.9017 High Similarity NPD8252 Approved
0.9017 High Similarity NPD8099 Discontinued
0.8966 High Similarity NPD8156 Discontinued
0.8556 High Similarity NPD8453 Clinical (unspecified phase)
0.8424 Intermediate Similarity NPD7906 Approved
0.8125 Intermediate Similarity NPD8095 Phase 1
0.8108 Intermediate Similarity NPD7313 Approved
0.8108 Intermediate Similarity NPD7312 Approved
0.8108 Intermediate Similarity NPD7311 Approved
0.8108 Intermediate Similarity NPD7310 Approved
0.8066 Intermediate Similarity NPD27 Approved
0.8066 Intermediate Similarity NPD2489 Approved
0.8065 Intermediate Similarity NPD7309 Approved
0.8056 Intermediate Similarity NPD3051 Approved
0.8011 Intermediate Similarity NPD4577 Approved
0.8011 Intermediate Similarity NPD4578 Approved
0.8011 Intermediate Similarity NPD2969 Approved
0.8011 Intermediate Similarity NPD2970 Approved
0.7979 Intermediate Similarity NPD4663 Approved
0.7965 Intermediate Similarity NPD2421 Approved
0.7965 Intermediate Similarity NPD2420 Approved
0.7919 Intermediate Similarity NPD4584 Approved
0.7877 Intermediate Similarity NPD6788 Approved
0.7833 Intermediate Similarity NPD7833 Phase 2
0.7833 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD7831 Phase 2
0.7692 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7663 Intermediate Similarity NPD6071 Discontinued
0.7654 Intermediate Similarity NPD4773 Phase 2
0.7654 Intermediate Similarity NPD4772 Phase 2
0.7611 Intermediate Similarity NPD7298 Approved
0.7588 Intermediate Similarity NPD3450 Approved
0.7588 Intermediate Similarity NPD3452 Approved
0.7588 Intermediate Similarity NPD2494 Approved
0.7588 Intermediate Similarity NPD2493 Approved
0.7581 Intermediate Similarity NPD4481 Phase 3
0.7577 Intermediate Similarity NPD2488 Approved
0.7577 Intermediate Similarity NPD2490 Approved
0.7554 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7447 Phase 1
0.7514 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD6997 Phase 2
0.7487 Intermediate Similarity NPD2898 Approved
0.7486 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD4583 Approved
0.7475 Intermediate Similarity NPD4582 Approved
0.7452 Intermediate Similarity NPD7047 Phase 3
0.7446 Intermediate Similarity NPD4055 Discovery
0.7432 Intermediate Similarity NPD2560 Approved
0.7432 Intermediate Similarity NPD2563 Approved
0.7426 Intermediate Similarity NPD4002 Approved
0.7426 Intermediate Similarity NPD4004 Approved
0.7401 Intermediate Similarity NPD3845 Phase 1
0.7387 Intermediate Similarity NPD2975 Approved
0.7387 Intermediate Similarity NPD2973 Approved
0.7387 Intermediate Similarity NPD2974 Approved
0.738 Intermediate Similarity NPD4010 Discontinued
0.736 Intermediate Similarity NPD7212 Phase 2
0.736 Intermediate Similarity NPD7213 Phase 3
0.7345 Intermediate Similarity NPD5241 Discontinued
0.7308 Intermediate Similarity NPD7827 Phase 1
0.7306 Intermediate Similarity NPD7549 Discontinued
0.7303 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD4580 Approved
0.7268 Intermediate Similarity NPD2971 Approved
0.7268 Intermediate Similarity NPD2968 Approved
0.7268 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD6031 Approved
0.7238 Intermediate Similarity NPD6030 Approved
0.7231 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD8153 Approved
0.7225 Intermediate Similarity NPD8152 Approved
0.7222 Intermediate Similarity NPD1424 Approved
0.7213 Intermediate Similarity NPD4675 Approved
0.7213 Intermediate Similarity NPD4678 Approved
0.7207 Intermediate Similarity NPD7124 Phase 2
0.7196 Intermediate Similarity NPD7907 Approved
0.7192 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD6042 Phase 2
0.7188 Intermediate Similarity NPD42 Phase 2
0.7181 Intermediate Similarity NPD5677 Discontinued
0.7174 Intermediate Similarity NPD6072 Discontinued
0.7158 Intermediate Similarity NPD4017 Approved
0.7143 Intermediate Similarity NPD7802 Discontinued
0.7143 Intermediate Similarity NPD3641 Approved
0.7143 Intermediate Similarity NPD3640 Phase 3
0.7143 Intermediate Similarity NPD3639 Approved
0.7136 Intermediate Similarity NPD4040 Phase 1
0.7088 Intermediate Similarity NPD6090 Discontinued
0.7074 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD7598 Phase 2
0.7065 Intermediate Similarity NPD4005 Discontinued
0.7059 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD6107 Approved
0.7027 Intermediate Similarity NPD6723 Discontinued
0.7026 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD5676 Approved
0.7011 Intermediate Similarity NPD4474 Approved
0.7011 Intermediate Similarity NPD4475 Approved
0.6973 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6971 Remote Similarity NPD3109 Approved
0.6971 Remote Similarity NPD3110 Approved
0.6959 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3057 Approved
0.6957 Remote Similarity NPD2122 Discontinued
0.6957 Remote Similarity NPD3448 Approved
0.6957 Remote Similarity NPD2491 Approved
0.6954 Remote Similarity NPD5718 Phase 2
0.6954 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6949 Remote Similarity NPD2200 Suspended
0.6944 Remote Similarity NPD5177 Phase 3
0.694 Remote Similarity NPD4123 Phase 3
0.6936 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6936 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7048 Phase 3
0.6923 Remote Similarity NPD6667 Approved
0.6923 Remote Similarity NPD6666 Approved
0.6915 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5772 Approved
0.6915 Remote Similarity NPD5773 Approved
0.6911 Remote Similarity NPD4666 Phase 3
0.6907 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6906 Remote Similarity NPD6748 Discontinued
0.6906 Remote Similarity NPD7466 Approved
0.6897 Remote Similarity NPD7262 Phase 1
0.6897 Remote Similarity NPD4625 Phase 3
0.6891 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6889 Remote Similarity NPD7037 Approved
0.6888 Remote Similarity NPD7479 Phase 2
0.6885 Remote Similarity NPD3124 Discontinued
0.6884 Remote Similarity NPD6853 Approved
0.6884 Remote Similarity NPD6851 Approved
0.6882 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6878 Remote Similarity NPD6284 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5006 Approved
0.6875 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2972 Approved
0.6875 Remote Similarity NPD3533 Approved
0.6875 Remote Similarity NPD5005 Approved
0.6875 Remote Similarity NPD1613 Approved
0.6872 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6866 Remote Similarity NPD4111 Phase 1
0.6866 Remote Similarity NPD4665 Approved
0.6859 Remote Similarity NPD5709 Phase 3
0.6857 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6854 Remote Similarity NPD7718 Clinical (unspecified phase)
0.6853 Remote Similarity NPD6297 Approved
0.6848 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4908 Phase 1
0.6837 Remote Similarity NPD5312 Approved
0.6837 Remote Similarity NPD5313 Approved
0.6837 Remote Similarity NPD4873 Discontinued
0.6824 Remote Similarity NPD6503 Clinical (unspecified phase)
0.6822 Remote Similarity NPD7169 Suspended
0.6818 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6816 Remote Similarity NPD1753 Discontinued
0.6812 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6811 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6811 Remote Similarity NPD3647 Clinical (unspecified phase)
0.6806 Remote Similarity NPD8005 Clinical (unspecified phase)
0.68 Remote Similarity NPD7922 Phase 1
0.68 Remote Similarity NPD5155 Approved
0.68 Remote Similarity NPD5156 Approved
0.6796 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7177 Discontinued
0.6784 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6782 Remote Similarity NPD7291 Discontinued
0.6776 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6776 Remote Similarity NPD5160 Discontinued
0.6776 Remote Similarity NPD3692 Discontinued
0.6774 Remote Similarity NPD5976 Discontinued
0.6772 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6763 Remote Similarity NPD4420 Approved
0.676 Remote Similarity NPD6111 Discontinued
0.676 Remote Similarity NPD6895 Approved
0.676 Remote Similarity NPD6896 Approved
0.6758 Remote Similarity NPD3060 Approved
0.6753 Remote Similarity NPD4166 Phase 2
0.6743 Remote Similarity NPD3594 Approved
0.6743 Remote Similarity NPD2606 Approved
0.6743 Remote Similarity NPD2605 Approved
0.6743 Remote Similarity NPD3595 Approved
0.674 Remote Similarity NPD4726 Approved
0.674 Remote Similarity NPD4725 Approved
0.674 Remote Similarity NPD2029 Clinical (unspecified phase)
0.674 Remote Similarity NPD4721 Approved
0.6739 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6737 Remote Similarity NPD2978 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