Structure

Physi-Chem Properties

Molecular Weight:  426.17
Volume:  429.874
LogP:  5.112
LogD:  3.158
LogS:  -3.694
# Rotatable Bonds:  4
TPSA:  109.36
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.539
Synthetic Accessibility Score:  3.889
Fsp3:  0.375
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.902
MDCK Permeability:  1.2040000001434237e-05
Pgp-inhibitor:  0.929
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.059
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  95.31500244140625%
Volume Distribution (VD):  0.614
Pgp-substrate:  7.706510066986084%

ADMET: Metabolism

CYP1A2-inhibitor:  0.287
CYP1A2-substrate:  0.929
CYP2C19-inhibitor:  0.21
CYP2C19-substrate:  0.382
CYP2C9-inhibitor:  0.825
CYP2C9-substrate:  0.909
CYP2D6-inhibitor:  0.445
CYP2D6-substrate:  0.304
CYP3A4-inhibitor:  0.193
CYP3A4-substrate:  0.175

ADMET: Excretion

Clearance (CL):  1.904
Half-life (T1/2):  0.245

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.776
Drug-inuced Liver Injury (DILI):  0.857
AMES Toxicity:  0.528
Rat Oral Acute Toxicity:  0.693
Maximum Recommended Daily Dose:  0.83
Skin Sensitization:  0.868
Carcinogencity:  0.469
Eye Corrosion:  0.003
Eye Irritation:  0.403
Respiratory Toxicity:  0.228

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

  Natural Product: NPC170245

Natural Product ID:  NPC170245
Common Name*:   11Alpha-Mangostanin
IUPAC Name:   (2R)-4,8-dihydroxy-2-(2-hydroxypropan-2-yl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrofuro[3,2-b]xanthen-5-one
Synonyms:   11Alpha-Mangostanin
Standard InCHIKey:  PDCFTPUXIGMZDM-GOSISDBHSA-N
Standard InCHI:  InChI=1S/C24H26O7/c1-11(2)6-7-12-19-16(9-14(25)23(12)29-5)30-17-10-15-13(21(26)20(17)22(19)27)8-18(31-15)24(3,4)28/h6,9-10,18,25-26,28H,7-8H2,1-5H3/t18-/m1/s1
SMILES:  CC(=CCc1c2c(cc(c1OC)O)oc1cc3c(C[C@H](C(C)(C)O)O3)c(c1c2=O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1080698
PubChem CID:   46880204
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones
                • [CHEMONTID:0003519] 8-prenylated xanthones

*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
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10075773]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. PMID[16933891]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18464091]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18558747]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota stem bark Pangradin village, Jasinga, West Java, Indonesia 2005-AUG PMID[19839614]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20817450]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. pericarp n.a. PMID[24555285]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[24717154]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota fruit hulls Madras, Tamil Nadu, India 1993-MAR PMID[9213587]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8560 Aplidium tabascum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8927 Poria selecta Species Coccinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9741 Actinopyga agassizi Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3707 Chromatium okenii Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27924 Serpocaulon triseriale Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25216 Senecio vellereus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9717 Wibelia divaricata Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4064 Halimodendron halodendron Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8354 Aster bellidiastrum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12600 Trametes cinnabarina Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3449 Lonicera hypoleuca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10221 Streptomyces alboniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10056 Nicotiana sylvestris Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7534 Leptogorgia sarmentosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24931 Myelochroa aurulenta Species Parmeliaceae 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
NPT139 Cell Line HT-29 Homo sapiens ED50 > 10.0 uM PMID[496829]

☑ 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 NPC170245 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9936 High Similarity NPC326520
0.9872 High Similarity NPC475985
0.9744 High Similarity NPC61010
0.9686 High Similarity NPC477154
0.9686 High Similarity NPC6588
0.9686 High Similarity NPC117854
0.9684 High Similarity NPC473286
0.9679 High Similarity NPC14353
0.9679 High Similarity NPC228785
0.9679 High Similarity NPC56085
0.962 High Similarity NPC248638
0.962 High Similarity NPC152659
0.962 High Similarity NPC236521
0.962 High Similarity NPC7483
0.9618 High Similarity NPC474186
0.9618 High Similarity NPC278052
0.9618 High Similarity NPC40491
0.9615 High Similarity NPC100123
0.9615 High Similarity NPC476242
0.956 High Similarity NPC239752
0.956 High Similarity NPC472450
0.956 High Similarity NPC275780
0.9557 High Similarity NPC81679
0.9557 High Similarity NPC25152
0.9554 High Similarity NPC320359
0.9554 High Similarity NPC475886
0.9554 High Similarity NPC36217
0.9554 High Similarity NPC474287
0.9554 High Similarity NPC472624
0.9551 High Similarity NPC217677
0.9551 High Similarity NPC223787
0.9551 High Similarity NPC241904
0.9551 High Similarity NPC300727
0.9551 High Similarity NPC165977
0.95 High Similarity NPC472452
0.95 High Similarity NPC39091
0.9497 High Similarity NPC189473
0.9497 High Similarity NPC473313
0.9497 High Similarity NPC18100
0.9497 High Similarity NPC236132
0.9497 High Similarity NPC197168
0.9497 High Similarity NPC23298
0.9497 High Similarity NPC186686
0.9497 High Similarity NPC220313
0.9497 High Similarity NPC273959
0.9497 High Similarity NPC124038
0.9497 High Similarity NPC41301
0.9497 High Similarity NPC329669
0.9497 High Similarity NPC472278
0.9494 High Similarity NPC474187
0.9494 High Similarity NPC474351
0.9494 High Similarity NPC475883
0.949 High Similarity NPC250214
0.949 High Similarity NPC95936
0.949 High Similarity NPC329091
0.9487 High Similarity NPC142339
0.9487 High Similarity NPC274730
0.9444 High Similarity NPC472276
0.9437 High Similarity NPC108433
0.9437 High Similarity NPC293319
0.9437 High Similarity NPC300053
0.9437 High Similarity NPC25361
0.9437 High Similarity NPC472277
0.9434 High Similarity NPC201800
0.9434 High Similarity NPC229632
0.9434 High Similarity NPC472402
0.9434 High Similarity NPC472635
0.943 High Similarity NPC200746
0.9427 High Similarity NPC156057
0.9427 High Similarity NPC48208
0.9427 High Similarity NPC162869
0.9427 High Similarity NPC78225
0.9427 High Similarity NPC236796
0.9427 High Similarity NPC474208
0.9427 High Similarity NPC27337
0.9427 High Similarity NPC36852
0.9427 High Similarity NPC474836
0.9427 High Similarity NPC475267
0.9427 High Similarity NPC469584
0.9427 High Similarity NPC136674
0.9427 High Similarity NPC262286
0.9423 High Similarity NPC45849
0.9423 High Similarity NPC200761
0.9423 High Similarity NPC470327
0.9423 High Similarity NPC477503
0.9383 High Similarity NPC288813
0.9383 High Similarity NPC152477
0.9379 High Similarity NPC37870
0.9379 High Similarity NPC472449
0.9379 High Similarity NPC43319
0.9379 High Similarity NPC235610
0.9379 High Similarity NPC173292
0.9375 High Similarity NPC472281
0.9375 High Similarity NPC270837
0.9375 High Similarity NPC205265
0.9375 High Similarity NPC146134
0.9371 High Similarity NPC266314
0.9371 High Similarity NPC32694
0.9371 High Similarity NPC134783
0.9367 High Similarity NPC85121
0.9367 High Similarity NPC210459
0.9363 High Similarity NPC470328
0.9363 High Similarity NPC472626
0.9363 High Similarity NPC235165
0.9363 High Similarity NPC278778
0.9363 High Similarity NPC195796
0.9363 High Similarity NPC35038
0.9363 High Similarity NPC68093
0.9363 High Similarity NPC138243
0.9363 High Similarity NPC24640
0.9363 High Similarity NPC191146
0.9363 High Similarity NPC291878
0.9363 High Similarity NPC209614
0.9363 High Similarity NPC255106
0.9359 High Similarity NPC74924
0.9359 High Similarity NPC89474
0.9341 High Similarity NPC150977
0.9329 High Similarity NPC310794
0.9321 High Similarity NPC218226
0.9321 High Similarity NPC126204
0.9321 High Similarity NPC474024
0.9321 High Similarity NPC150131
0.9317 High Similarity NPC224280
0.9317 High Similarity NPC62261
0.9317 High Similarity NPC37183
0.9317 High Similarity NPC475888
0.9313 High Similarity NPC472964
0.9313 High Similarity NPC472448
0.9313 High Similarity NPC294965
0.9313 High Similarity NPC474162
0.9313 High Similarity NPC83922
0.9313 High Similarity NPC211107
0.9313 High Similarity NPC474150
0.9313 High Similarity NPC329760
0.9313 High Similarity NPC52204
0.9308 High Similarity NPC235018
0.9308 High Similarity NPC472630
0.9308 High Similarity NPC174953
0.9308 High Similarity NPC321399
0.9308 High Similarity NPC472902
0.9308 High Similarity NPC45146
0.9308 High Similarity NPC472631
0.9308 High Similarity NPC192686
0.9308 High Similarity NPC139036
0.9308 High Similarity NPC470810
0.9308 High Similarity NPC204290
0.9308 High Similarity NPC299436
0.9308 High Similarity NPC471973
0.9308 High Similarity NPC476980
0.9308 High Similarity NPC80375
0.9308 High Similarity NPC119209
0.9308 High Similarity NPC328102
0.9308 High Similarity NPC119224
0.9308 High Similarity NPC118256
0.9304 High Similarity NPC472914
0.9304 High Similarity NPC472913
0.9304 High Similarity NPC245758
0.9304 High Similarity NPC99597
0.9304 High Similarity NPC472598
0.9304 High Similarity NPC222814
0.9304 High Similarity NPC210084
0.9304 High Similarity NPC472910
0.9304 High Similarity NPC472911
0.9304 High Similarity NPC291508
0.9304 High Similarity NPC474055
0.9304 High Similarity NPC96167
0.9299 High Similarity NPC113906
0.9299 High Similarity NPC67396
0.9299 High Similarity NPC37392
0.9295 High Similarity NPC106976
0.9268 High Similarity NPC121333
0.9264 High Similarity NPC242395
0.9259 High Similarity NPC120593
0.9259 High Similarity NPC128293
0.9259 High Similarity NPC277480
0.9259 High Similarity NPC119589
0.9255 High Similarity NPC474240
0.9255 High Similarity NPC133065
0.9255 High Similarity NPC474350
0.9255 High Similarity NPC207690
0.925 High Similarity NPC167678
0.925 High Similarity NPC471210
0.925 High Similarity NPC471211
0.925 High Similarity NPC29876
0.925 High Similarity NPC66288
0.925 High Similarity NPC472634
0.925 High Similarity NPC474038
0.925 High Similarity NPC472632
0.925 High Similarity NPC471212
0.9245 High Similarity NPC235448
0.9245 High Similarity NPC152904
0.9245 High Similarity NPC474290
0.9245 High Similarity NPC473990
0.9241 High Similarity NPC472916
0.9236 High Similarity NPC18727
0.9236 High Similarity NPC298692
0.9236 High Similarity NPC213896
0.9236 High Similarity NPC192083
0.9231 High Similarity NPC202157
0.9207 High Similarity NPC101107

  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 NPC170245 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 NPD2393 Clinical (unspecified phase)
0.9172 High Similarity NPD1934 Approved
0.9114 High Similarity NPD2801 Approved
0.9068 High Similarity NPD5494 Approved
0.8882 High Similarity NPD3882 Suspended
0.8743 High Similarity NPD3818 Discontinued
0.8735 High Similarity NPD6168 Clinical (unspecified phase)
0.8735 High Similarity NPD6166 Phase 2
0.8735 High Similarity NPD6167 Clinical (unspecified phase)
0.858 High Similarity NPD5844 Phase 1
0.8544 High Similarity NPD1511 Approved
0.8537 High Similarity NPD4868 Clinical (unspecified phase)
0.8529 High Similarity NPD7074 Phase 3
0.8503 High Similarity NPD6232 Discontinued
0.8488 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8471 Intermediate Similarity NPD7054 Approved
0.8462 Intermediate Similarity NPD7473 Discontinued
0.8457 Intermediate Similarity NPD4380 Phase 2
0.8443 Intermediate Similarity NPD6959 Discontinued
0.8438 Intermediate Similarity NPD1512 Approved
0.8421 Intermediate Similarity NPD7472 Approved
0.8415 Intermediate Similarity NPD7819 Suspended
0.8375 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD7075 Discontinued
0.8364 Intermediate Similarity NPD3817 Phase 2
0.8303 Intermediate Similarity NPD1465 Phase 2
0.8303 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8266 Intermediate Similarity NPD6797 Phase 2
0.8261 Intermediate Similarity NPD2534 Approved
0.8261 Intermediate Similarity NPD2533 Approved
0.8261 Intermediate Similarity NPD2532 Approved
0.8253 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD1549 Phase 2
0.8225 Intermediate Similarity NPD1247 Approved
0.8218 Intermediate Similarity NPD7251 Discontinued
0.8171 Intermediate Similarity NPD7808 Phase 3
0.8155 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD6559 Discontinued
0.8107 Intermediate Similarity NPD6234 Discontinued
0.8063 Intermediate Similarity NPD2800 Approved
0.8057 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD3749 Approved
0.8046 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD6801 Discontinued
0.8 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD2796 Approved
0.7964 Intermediate Similarity NPD7411 Suspended
0.7933 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD5402 Approved
0.7925 Intermediate Similarity NPD1510 Phase 2
0.7919 Intermediate Similarity NPD3926 Phase 2
0.7917 Intermediate Similarity NPD37 Approved
0.7912 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD919 Approved
0.7888 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD7228 Approved
0.7882 Intermediate Similarity NPD4967 Phase 2
0.7882 Intermediate Similarity NPD4965 Approved
0.7882 Intermediate Similarity NPD4966 Approved
0.7866 Intermediate Similarity NPD6799 Approved
0.7807 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD7199 Phase 2
0.7798 Intermediate Similarity NPD6599 Discontinued
0.7785 Intermediate Similarity NPD943 Approved
0.7785 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD1240 Approved
0.7785 Intermediate Similarity NPD1613 Approved
0.7784 Intermediate Similarity NPD3751 Discontinued
0.7771 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD2935 Discontinued
0.7759 Intermediate Similarity NPD3787 Discontinued
0.7759 Intermediate Similarity NPD5710 Approved
0.7759 Intermediate Similarity NPD5711 Approved
0.7714 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD1607 Approved
0.7683 Intermediate Similarity NPD3750 Approved
0.7674 Intermediate Similarity NPD7768 Phase 2
0.7654 Intermediate Similarity NPD6100 Approved
0.7654 Intermediate Similarity NPD6099 Approved
0.7643 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD3226 Approved
0.7625 Intermediate Similarity NPD230 Phase 1
0.7619 Intermediate Similarity NPD6776 Approved
0.7619 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD6781 Approved
0.7619 Intermediate Similarity NPD6779 Approved
0.7619 Intermediate Similarity NPD6780 Approved
0.7619 Intermediate Similarity NPD920 Approved
0.7619 Intermediate Similarity NPD6782 Approved
0.7619 Intermediate Similarity NPD6778 Approved
0.7619 Intermediate Similarity NPD6777 Approved
0.7607 Intermediate Similarity NPD2346 Discontinued
0.7596 Intermediate Similarity NPD8434 Phase 2
0.7595 Intermediate Similarity NPD3027 Phase 3
0.7593 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7390 Discontinued
0.7527 Intermediate Similarity NPD8312 Approved
0.7527 Intermediate Similarity NPD8313 Approved
0.7515 Intermediate Similarity NPD1243 Approved
0.7515 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD5403 Approved
0.75 Intermediate Similarity NPD2344 Approved
0.75 Intermediate Similarity NPD7435 Discontinued
0.75 Intermediate Similarity NPD8150 Discontinued
0.75 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD1653 Approved
0.747 Intermediate Similarity NPD4628 Phase 3
0.7458 Intermediate Similarity NPD7229 Phase 3
0.744 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD6190 Approved
0.7418 Intermediate Similarity NPD7240 Approved
0.7418 Intermediate Similarity NPD7685 Pre-registration
0.7411 Intermediate Similarity NPD7783 Phase 2
0.7411 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD7696 Phase 3
0.7409 Intermediate Similarity NPD7697 Approved
0.7409 Intermediate Similarity NPD7698 Approved
0.7407 Intermediate Similarity NPD447 Suspended
0.7398 Intermediate Similarity NPD8151 Discontinued
0.7396 Intermediate Similarity NPD5401 Approved
0.7381 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD3748 Approved
0.7378 Intermediate Similarity NPD2799 Discontinued
0.7375 Intermediate Similarity NPD4625 Phase 3
0.7371 Intermediate Similarity NPD7871 Phase 2
0.7371 Intermediate Similarity NPD7870 Phase 2
0.7365 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD5953 Discontinued
0.7362 Intermediate Similarity NPD6651 Approved
0.7358 Intermediate Similarity NPD6823 Phase 2
0.7354 Intermediate Similarity NPD6535 Approved
0.7354 Intermediate Similarity NPD6534 Approved
0.7348 Intermediate Similarity NPD7286 Phase 2
0.7347 Intermediate Similarity NPD7701 Phase 2
0.7333 Intermediate Similarity NPD1551 Phase 2
0.7329 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD2309 Approved
0.7306 Intermediate Similarity NPD2494 Approved
0.7306 Intermediate Similarity NPD2493 Approved
0.7278 Intermediate Similarity NPD2403 Approved
0.7273 Intermediate Similarity NPD7874 Approved
0.7273 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD4360 Phase 2
0.7263 Intermediate Similarity NPD4363 Phase 3
0.7255 Intermediate Similarity NPD7907 Approved
0.725 Intermediate Similarity NPD2861 Phase 2
0.725 Intermediate Similarity NPD9494 Approved
0.7246 Intermediate Similarity NPD2424 Discontinued
0.7241 Intermediate Similarity NPD4111 Phase 1
0.7241 Intermediate Similarity NPD4665 Approved
0.724 Intermediate Similarity NPD7699 Phase 2
0.724 Intermediate Similarity NPD7700 Phase 2
0.7236 Intermediate Similarity NPD7801 Approved
0.7225 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2313 Discontinued
0.7222 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD3452 Approved
0.7216 Intermediate Similarity NPD3450 Approved
0.7205 Intermediate Similarity NPD4908 Phase 1
0.7204 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD1933 Approved
0.7194 Intermediate Similarity NPD4583 Approved
0.7194 Intermediate Similarity NPD4582 Approved
0.7193 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD7033 Discontinued
0.716 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD5760 Phase 2
0.7159 Intermediate Similarity NPD5761 Phase 2
0.7143 Intermediate Similarity NPD4002 Approved
0.7143 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4004 Approved
0.7143 Intermediate Similarity NPD4287 Approved
0.7135 Intermediate Similarity NPD4361 Phase 2
0.7135 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD4060 Phase 1
0.7127 Intermediate Similarity NPD5242 Approved
0.7121 Intermediate Similarity NPD7584 Approved
0.7119 Intermediate Similarity NPD5353 Approved
0.7117 Intermediate Similarity NPD3764 Approved
0.7113 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD6844 Discontinued
0.7101 Intermediate Similarity NPD6674 Discontinued
0.7101 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD2974 Approved
0.7098 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD2975 Approved
0.7098 Intermediate Similarity NPD2973 Approved
0.7092 Intermediate Similarity NPD5006 Approved
0.7092 Intermediate Similarity NPD5005 Approved
0.7089 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1610 Phase 2

  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