Structure

Physi-Chem Properties

Molecular Weight:  608.29
Volume:  631.71
LogP:  6.147
LogD:  3.861
LogS:  -6.119
# Rotatable Bonds:  4
TPSA:  70.65
# H-Bond Aceptor:  8
# H-Bond Donor:  1
# Rings:  8
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.271
Synthetic Accessibility Score:  5.758
Fsp3:  0.351
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Rejected
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:  -5.911
MDCK Permeability:  2.2091218852438033e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.987
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.07
30% Bioavailability (F30%):  0.914

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.059
Plasma Protein Binding (PPB):  62.19306945800781%
Volume Distribution (VD):  0.71
Pgp-substrate:  15.215185165405273%

ADMET: Metabolism

CYP1A2-inhibitor:  0.056
CYP1A2-substrate:  0.958
CYP2C19-inhibitor:  0.195
CYP2C19-substrate:  0.959
CYP2C9-inhibitor:  0.044
CYP2C9-substrate:  0.597
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.959
CYP3A4-inhibitor:  0.167
CYP3A4-substrate:  0.954

ADMET: Excretion

Clearance (CL):  7.247
Half-life (T1/2):  0.164

ADMET: Toxicity

hERG Blockers:  0.97
Human Hepatotoxicity (H-HT):  0.06
Drug-inuced Liver Injury (DILI):  0.756
AMES Toxicity:  0.098
Rat Oral Acute Toxicity:  0.505
Maximum Recommended Daily Dose:  0.995
Skin Sensitization:  0.588
Carcinogencity:  0.026
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.403

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

  Natural Product: NPC475479

Natural Product ID:  NPC475479
Common Name*:   ULYPVLZRRZENPT-WDYNHAJCSA-N
IUPAC Name:   n.a.
Synonyms:   (+)-2-Norobaberine
Standard InCHIKey:  ULYPVLZRRZENPT-WDYNHAJCSA-N
Standard InCHI:  InChI=1S/C37H40N2O6/c1-39-15-13-25-20-34(42-4)36(43-5)37-35(25)29(39)17-22-6-9-26(10-7-22)44-32-18-23(8-11-30(32)40-2)16-28-27-21-33(45-37)31(41-3)19-24(27)12-14-38-28/h6-11,18-21,28-29,38H,12-17H2,1-5H3/t28-,29+/m1/s1
SMILES:  CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=CC(=C(C=C7CCN6)OC)O3)OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL506363
PubChem CID:   21582958
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO26964 Stephania erecta Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[8450319]
NPO26964 Stephania erecta Species Menispermaceae Eukaryota tubers n.a. n.a. PMID[8450319]
NPO26964 Stephania erecta Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26964 Stephania erecta Species Menispermaceae Eukaryota tubers n.a. n.a. Database[PMID; Title]
NPO32960 stephania pierrii Species Menispermaceae Eukaryota tubers n.a. n.a. Database[PMID; Title]
NPO26964 Stephania erecta Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26964 Stephania erecta Species Menispermaceae 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
NPT453 Cell Line HT-1080 Homo sapiens ED50 = 7.4 ug ml-1 PMID[495411]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 14.5 ug ml-1 PMID[495411]
NPT91 Cell Line KB Homo sapiens ED50 = 6.0 ug ml-1 PMID[495411]
NPT168 Cell Line P388 Mus musculus ED50 = 3.5 ug ml-1 PMID[495411]
NPT762 Cell Line A-431 Homo sapiens ED50 = 6.1 ug ml-1 PMID[495411]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 3.7 ug ml-1 PMID[495411]
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 1.2 ug ml-1 PMID[495411]
NPT91 Cell Line KB Homo sapiens ED50 = 9900.0 nM PMID[495412]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 45.9 ng/ml PMID[495411]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum ED50 = 93.7 ng/ml PMID[495411]
NPT27 Others Unspecified ED50 = 3.2 ug ml-1 PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 70.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 34.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 161.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 79.0 n.a. PMID[495411]
NPT27 Others Unspecified ED50 = 9.7 ug ml-1 PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 192.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 94.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 316.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 155.0 n.a. PMID[495411]
NPT27 Others Unspecified ED50 = 5.5 ug ml-1 PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 120.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 17.4 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 131.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 64.0 n.a. PMID[495411]
NPT27 Others Unspecified ED50 = 2.0 ug ml-1 PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 44.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 21.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 76.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 37.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 133.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 65.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 81.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 40.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 41.0 n.a. PMID[495411]
NPT2 Others Unspecified Ratio ED50 = 20.0 n.a. PMID[495411]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 75.0 nM PMID[495412]
NPT2 Others Unspecified Selectivity Index = 130.0 n.a. PMID[495412]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 154.0 nM PMID[495412]
NPT2 Others Unspecified Selectivity Index = 64.0 n.a. PMID[495412]

☑ 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 NPC475479 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 NPC243454
0.9939 High Similarity NPC239584
0.9691 High Similarity NPC317145
0.9691 High Similarity NPC115284
0.9691 High Similarity NPC317439
0.9691 High Similarity NPC76682
0.9691 High Similarity NPC227060
0.9691 High Similarity NPC10908
0.9691 High Similarity NPC276890
0.9691 High Similarity NPC63646
0.9691 High Similarity NPC198498
0.9632 High Similarity NPC12424
0.9632 High Similarity NPC129518
0.9632 High Similarity NPC41376
0.9632 High Similarity NPC251580
0.9586 High Similarity NPC274661
0.9586 High Similarity NPC281581
0.9586 High Similarity NPC11296
0.9586 High Similarity NPC175890
0.9586 High Similarity NPC48490
0.9586 High Similarity NPC82457
0.9529 High Similarity NPC60295
0.9529 High Similarity NPC191132
0.9515 High Similarity NPC293093
0.9419 High Similarity NPC256124
0.9321 High Similarity NPC475393
0.929 High Similarity NPC104196
0.929 High Similarity NPC8836
0.929 High Similarity NPC181796
0.929 High Similarity NPC182052
0.929 High Similarity NPC271013
0.929 High Similarity NPC7715
0.929 High Similarity NPC217748
0.929 High Similarity NPC73492
0.929 High Similarity NPC239824
0.929 High Similarity NPC42663
0.929 High Similarity NPC223690
0.929 High Similarity NPC290582
0.929 High Similarity NPC222661
0.929 High Similarity NPC229373
0.929 High Similarity NPC311973
0.929 High Similarity NPC258657
0.929 High Similarity NPC251735
0.929 High Similarity NPC328155
0.929 High Similarity NPC49075
0.929 High Similarity NPC15414
0.929 High Similarity NPC290005
0.929 High Similarity NPC279228
0.929 High Similarity NPC54654
0.929 High Similarity NPC185639
0.929 High Similarity NPC299990
0.929 High Similarity NPC90998
0.929 High Similarity NPC285931
0.9235 High Similarity NPC274716
0.9235 High Similarity NPC254441
0.9235 High Similarity NPC167116
0.9231 High Similarity NPC286119
0.9181 High Similarity NPC302245
0.9181 High Similarity NPC95426
0.9181 High Similarity NPC16357
0.9176 High Similarity NPC30779
0.9128 High Similarity NPC212237
0.9128 High Similarity NPC139783
0.9128 High Similarity NPC65312
0.9128 High Similarity NPC116465
0.9123 High Similarity NPC302275
0.9075 High Similarity NPC22115
0.9075 High Similarity NPC275680
0.907 High Similarity NPC249996
0.9023 High Similarity NPC206900
0.9012 High Similarity NPC247639
0.9012 High Similarity NPC25084
0.9006 High Similarity NPC195538
0.8971 High Similarity NPC473716
0.8971 High Similarity NPC475597
0.8953 High Similarity NPC476202
0.892 High Similarity NPC24260
0.8908 High Similarity NPC47077
0.8908 High Similarity NPC14507
0.8876 High Similarity NPC475215
0.8876 High Similarity NPC108434
0.8814 High Similarity NPC478093
0.8765 High Similarity NPC10871
0.8764 High Similarity NPC473589
0.8764 High Similarity NPC478091
0.8764 High Similarity NPC478092
0.8764 High Similarity NPC30182
0.8698 High Similarity NPC204947
0.8659 High Similarity NPC85381
0.8652 High Similarity NPC41122
0.8652 High Similarity NPC318805
0.8639 High Similarity NPC13916
0.8639 High Similarity NPC264850
0.8639 High Similarity NPC250846
0.8639 High Similarity NPC42549
0.8639 High Similarity NPC256012
0.8639 High Similarity NPC268503
0.8639 High Similarity NPC240841
0.8639 High Similarity NPC317272
0.8626 High Similarity NPC475654
0.8606 High Similarity NPC80129
0.8606 High Similarity NPC187022
0.858 High Similarity NPC24465
0.8571 High Similarity NPC257269
0.8571 High Similarity NPC230276
0.8564 High Similarity NPC234318
0.8563 High Similarity NPC7393
0.8538 High Similarity NPC83198
0.8538 High Similarity NPC204908
0.8519 High Similarity NPC106295
0.8519 High Similarity NPC210437
0.8519 High Similarity NPC476144
0.8519 High Similarity NPC51957
0.8519 High Similarity NPC16107
0.8514 High Similarity NPC119068
0.8514 High Similarity NPC40496
0.8486 Intermediate Similarity NPC254581
0.8466 Intermediate Similarity NPC7467
0.8409 Intermediate Similarity NPC474507
0.8391 Intermediate Similarity NPC190783
0.8391 Intermediate Similarity NPC232386
0.8391 Intermediate Similarity NPC152680
0.8383 Intermediate Similarity NPC123323
0.8362 Intermediate Similarity NPC32413
0.8362 Intermediate Similarity NPC474506
0.8352 Intermediate Similarity NPC23219
0.8314 Intermediate Similarity NPC56887
0.8314 Intermediate Similarity NPC223077
0.8314 Intermediate Similarity NPC193853
0.8305 Intermediate Similarity NPC258695
0.8305 Intermediate Similarity NPC470879
0.8295 Intermediate Similarity NPC476577
0.8295 Intermediate Similarity NPC112575
0.8295 Intermediate Similarity NPC173416
0.8295 Intermediate Similarity NPC148709
0.8276 Intermediate Similarity NPC109925
0.8272 Intermediate Similarity NPC476567
0.8272 Intermediate Similarity NPC128019
0.8272 Intermediate Similarity NPC136860
0.8263 Intermediate Similarity NPC114124
0.8256 Intermediate Similarity NPC121275
0.8256 Intermediate Similarity NPC209377
0.8256 Intermediate Similarity NPC4138
0.8256 Intermediate Similarity NPC284183
0.8225 Intermediate Similarity NPC170503
0.8225 Intermediate Similarity NPC203784
0.8225 Intermediate Similarity NPC126519
0.8176 Intermediate Similarity NPC476572
0.8166 Intermediate Similarity NPC99659
0.8166 Intermediate Similarity NPC204828
0.8166 Intermediate Similarity NPC138487
0.8166 Intermediate Similarity NPC325871
0.8166 Intermediate Similarity NPC216459
0.8166 Intermediate Similarity NPC5238
0.8166 Intermediate Similarity NPC249797
0.8166 Intermediate Similarity NPC110416
0.8166 Intermediate Similarity NPC469817
0.8166 Intermediate Similarity NPC295691
0.8166 Intermediate Similarity NPC193949
0.8166 Intermediate Similarity NPC172765
0.8166 Intermediate Similarity NPC54379
0.8166 Intermediate Similarity NPC127674
0.8166 Intermediate Similarity NPC39701
0.8166 Intermediate Similarity NPC189266
0.8166 Intermediate Similarity NPC207757
0.8166 Intermediate Similarity NPC278799
0.8166 Intermediate Similarity NPC2413
0.8166 Intermediate Similarity NPC184026
0.8166 Intermediate Similarity NPC41178
0.8166 Intermediate Similarity NPC276588
0.8148 Intermediate Similarity NPC188163
0.8148 Intermediate Similarity NPC213206
0.8148 Intermediate Similarity NPC328750
0.8148 Intermediate Similarity NPC474915
0.8142 Intermediate Similarity NPC475754
0.8125 Intermediate Similarity NPC239775
0.8125 Intermediate Similarity NPC19520
0.8125 Intermediate Similarity NPC149090
0.8118 Intermediate Similarity NPC146288
0.8107 Intermediate Similarity NPC477564
0.8107 Intermediate Similarity NPC2295
0.8098 Intermediate Similarity NPC476565
0.8086 Intermediate Similarity NPC314682
0.8084 Intermediate Similarity NPC207824
0.8084 Intermediate Similarity NPC92541
0.8084 Intermediate Similarity NPC60538
0.8081 Intermediate Similarity NPC230956
0.8081 Intermediate Similarity NPC271388
0.8081 Intermediate Similarity NPC205255
0.8081 Intermediate Similarity NPC235143
0.8081 Intermediate Similarity NPC119649
0.8079 Intermediate Similarity NPC66341
0.8079 Intermediate Similarity NPC192135
0.8079 Intermediate Similarity NPC477020
0.8077 Intermediate Similarity NPC57036
0.8068 Intermediate Similarity NPC69712
0.8068 Intermediate Similarity NPC477562
0.8068 Intermediate Similarity NPC168753
0.8068 Intermediate Similarity NPC26240
0.8068 Intermediate Similarity NPC6152

  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 NPC475479 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
0.9691 High Similarity NPD8251 Approved
0.9691 High Similarity NPD8099 Discontinued
0.9691 High Similarity NPD8252 Approved
0.9632 High Similarity NPD8156 Discontinued
0.929 High Similarity NPD8053 Approved
0.929 High Similarity NPD8054 Approved
0.8674 High Similarity NPD8095 Phase 1
0.8606 High Similarity NPD7298 Approved
0.8519 High Similarity NPD4584 Approved
0.8514 High Similarity NPD8453 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD6788 Approved
0.8293 Intermediate Similarity NPD1424 Approved
0.8193 Intermediate Similarity NPD6030 Approved
0.8193 Intermediate Similarity NPD6031 Approved
0.8148 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD6107 Approved
0.7904 Intermediate Similarity NPD7598 Phase 2
0.7895 Intermediate Similarity NPD4772 Phase 2
0.7895 Intermediate Similarity NPD4773 Phase 2
0.7819 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD6071 Discontinued
0.7679 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD7124 Phase 2
0.7614 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD4585 Approved
0.7598 Intermediate Similarity NPD3051 Approved
0.7594 Intermediate Similarity NPD7906 Approved
0.7584 Intermediate Similarity NPD5677 Discontinued
0.7584 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD4017 Approved
0.7571 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD7833 Phase 2
0.7571 Intermediate Similarity NPD7831 Phase 2
0.7558 Intermediate Similarity NPD3640 Phase 3
0.7558 Intermediate Similarity NPD3639 Approved
0.7558 Intermediate Similarity NPD3641 Approved
0.7542 Intermediate Similarity NPD7802 Discontinued
0.7514 Intermediate Similarity NPD4481 Phase 3
0.75 Intermediate Similarity NPD4166 Phase 2
0.75 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD4055 Discovery
0.7459 Intermediate Similarity NPD2969 Approved
0.7459 Intermediate Similarity NPD2970 Approved
0.7458 Intermediate Similarity NPD2560 Approved
0.7458 Intermediate Similarity NPD2563 Approved
0.7457 Intermediate Similarity NPD5976 Discontinued
0.7442 Intermediate Similarity NPD7447 Phase 1
0.7439 Intermediate Similarity NPD4475 Approved
0.7439 Intermediate Similarity NPD4474 Approved
0.7433 Intermediate Similarity NPD6851 Approved
0.7433 Intermediate Similarity NPD6853 Approved
0.7419 Intermediate Similarity NPD7549 Discontinued
0.7412 Intermediate Similarity NPD6748 Discontinued
0.7405 Intermediate Similarity NPD6297 Approved
0.738 Intermediate Similarity NPD7310 Approved
0.738 Intermediate Similarity NPD7312 Approved
0.738 Intermediate Similarity NPD7311 Approved
0.738 Intermediate Similarity NPD7313 Approved
0.7378 Intermediate Similarity NPD5718 Phase 2
0.7365 Intermediate Similarity NPD2200 Suspended
0.7362 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD4162 Approved
0.7345 Intermediate Similarity NPD3382 Approved
0.7345 Intermediate Similarity NPD3383 Approved
0.7345 Intermediate Similarity NPD3384 Approved
0.734 Intermediate Similarity NPD7309 Approved
0.734 Intermediate Similarity NPD6618 Phase 2
0.7326 Intermediate Similarity NPD3845 Phase 1
0.7322 Intermediate Similarity NPD27 Approved
0.7322 Intermediate Similarity NPD2489 Approved
0.7312 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD5006 Approved
0.731 Intermediate Similarity NPD7466 Approved
0.731 Intermediate Similarity NPD5005 Approved
0.7297 Intermediate Similarity NPD5312 Approved
0.7297 Intermediate Similarity NPD5313 Approved
0.7287 Intermediate Similarity NPD4577 Approved
0.7287 Intermediate Similarity NPD4578 Approved
0.7283 Intermediate Similarity NPD7213 Phase 3
0.7283 Intermediate Similarity NPD7212 Phase 2
0.7283 Intermediate Similarity NPD3124 Discontinued
0.7273 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD5160 Discontinued
0.7263 Intermediate Similarity NPD4663 Approved
0.7247 Intermediate Similarity NPD5720 Discontinued
0.7241 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD4678 Approved
0.7232 Intermediate Similarity NPD4675 Approved
0.7204 Intermediate Similarity NPD42 Phase 2
0.7204 Intermediate Similarity NPD6042 Phase 2
0.7196 Intermediate Similarity NPD2971 Approved
0.7196 Intermediate Similarity NPD2968 Approved
0.7176 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD4005 Discontinued
0.7168 Intermediate Similarity NPD2677 Approved
0.7168 Intermediate Similarity NPD5241 Discontinued
0.7162 Intermediate Similarity NPD8152 Approved
0.7162 Intermediate Similarity NPD8153 Approved
0.716 Intermediate Similarity NPD6895 Approved
0.716 Intermediate Similarity NPD6896 Approved
0.716 Intermediate Similarity NPD6111 Discontinued
0.7151 Intermediate Similarity NPD3060 Approved
0.7143 Intermediate Similarity NPD6621 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD3532 Approved
0.7126 Intermediate Similarity NPD3531 Approved
0.7126 Intermediate Similarity NPD3530 Approved
0.7126 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD4010 Discontinued
0.712 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4420 Approved
0.7097 Intermediate Similarity NPD3489 Phase 3
0.7095 Intermediate Similarity NPD6072 Discontinued
0.7088 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD1774 Approved
0.7074 Intermediate Similarity NPD7479 Phase 2
0.7073 Intermediate Similarity NPD7827 Phase 1
0.7069 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD2974 Approved
0.7056 Intermediate Similarity NPD5722 Discontinued
0.7056 Intermediate Similarity NPD2973 Approved
0.7056 Intermediate Similarity NPD2975 Approved
0.7047 Intermediate Similarity NPD7291 Discontinued
0.7043 Intermediate Similarity NPD2898 Approved
0.7018 Intermediate Similarity NPD2155 Approved
0.7018 Intermediate Similarity NPD2154 Approved
0.7018 Intermediate Similarity NPD2156 Approved
0.7017 Intermediate Similarity NPD5773 Approved
0.7017 Intermediate Similarity NPD5772 Approved
0.7017 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD52 Approved
0.7006 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7526 Approved
0.7005 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2653 Approved
0.6994 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7153 Discontinued
0.6989 Remote Similarity NPD2420 Approved
0.6989 Remote Similarity NPD2421 Approved
0.6985 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6983 Remote Similarity NPD6523 Clinical (unspecified phase)
0.697 Remote Similarity NPD7034 Discontinued
0.6968 Remote Similarity NPD5940 Clinical (unspecified phase)
0.6966 Remote Similarity NPD2122 Discontinued
0.6964 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6963 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5709 Phase 3
0.6954 Remote Similarity NPD5177 Phase 3
0.695 Remote Similarity NPD4580 Approved
0.6949 Remote Similarity NPD4123 Phase 3
0.6946 Remote Similarity NPD3537 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2977 Approved
0.6923 Remote Similarity NPD2845 Phase 2
0.6923 Remote Similarity NPD2978 Approved
0.6923 Remote Similarity NPD2843 Phase 2
0.6923 Remote Similarity NPD554 Clinical (unspecified phase)
0.6919 Remote Similarity NPD4666 Phase 3
0.6915 Remote Similarity NPD2494 Approved
0.6915 Remote Similarity NPD3452 Approved
0.6915 Remote Similarity NPD3450 Approved
0.6915 Remote Similarity NPD2493 Approved
0.6909 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6906 Remote Similarity NPD5090 Approved
0.6906 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6906 Remote Similarity NPD7110 Phase 1
0.6906 Remote Similarity NPD5089 Approved
0.6898 Remote Similarity NPD5242 Approved
0.6893 Remote Similarity NPD6087 Phase 1
0.6888 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6888 Remote Similarity NPD2488 Approved
0.6888 Remote Similarity NPD2490 Approved
0.6882 Remote Similarity NPD3109 Approved
0.6882 Remote Similarity NPD3110 Approved
0.6879 Remote Similarity NPD3156 Discontinued
0.6878 Remote Similarity NPD5708 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4727 Phase 1
0.6872 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6868 Remote Similarity NPD1769 Discontinued
0.6866 Remote Similarity NPD5457 Discontinued
0.6866 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6864 Remote Similarity NPD1336 Approved
0.6857 Remote Similarity NPD2458 Approved
0.6857 Remote Similarity NPD2460 Phase 3
0.6857 Remote Similarity NPD5062 Approved
0.6857 Remote Similarity NPD4236 Phase 3
0.6857 Remote Similarity NPD2459 Approved
0.6857 Remote Similarity NPD5061 Approved
0.6857 Remote Similarity NPD4237 Approved
0.6854 Remote Similarity NPD2874 Phase 2
0.6854 Remote Similarity NPD1771 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