Structure

Physi-Chem Properties

Molecular Weight:  682.26
Volume:  667.782
LogP:  0.702
LogD:  0.203
LogS:  -2.928
# Rotatable Bonds:  8
TPSA:  203.19
# H-Bond Aceptor:  13
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.129
Synthetic Accessibility Score:  7.351
Fsp3:  0.583
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  3
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.502
MDCK Permeability:  3.5215693060308695e-05
Pgp-inhibitor:  0.693
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.991
20% Bioavailability (F20%):  0.988
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  80.9663314819336%
Volume Distribution (VD):  0.937
Pgp-substrate:  11.778824806213379%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.113
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.074
CYP2C9-inhibitor:  0.114
CYP2C9-substrate:  0.038
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.073
CYP3A4-inhibitor:  0.523
CYP3A4-substrate:  0.257

ADMET: Excretion

Clearance (CL):  1.3
Half-life (T1/2):  0.238

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.194
Drug-inuced Liver Injury (DILI):  0.267
AMES Toxicity:  0.197
Rat Oral Acute Toxicity:  0.896
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.772
Carcinogencity:  0.878
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.971

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

  Natural Product: NPC475309

Natural Product ID:  NPC475309
Common Name*:   ZEETYDSXZRFRER-VTOZHPRFSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ZEETYDSXZRFRER-VTOZHPRFSA-N
Standard InCHI:  InChI=1S/C36H42O13/c1-16-9-24(39)27-22(13-37)7-5-20(11-35(16,27)45)18(3)32(43)48-31-26(14-38)47-34(30(42)29(31)41)46-15-23-8-6-21-12-36(49-33(44)19(21)4)17(2)10-25(40)28(23)36/h9-10,20-21,26,29-31,34,37-38,41-42,45H,3-8,11-15H2,1-2H3/t20-,21-,26+,29+,30+,31+,34+,35+,36+/m1/s1
SMILES:  CC1=CC(=O)C2=C(CCC(CC12O)C(=C)C(=O)OC3C(OC(C(C3O)O)OCC4=C5C(=O)C=C(C56CC(CC4)C(=C)C(=O)O6)C)CO)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503318
PubChem CID:   44566325
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003918] Saccharolipids

*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
NPO32466 leontodon hispidus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[10425121]

☑ 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
NPT762 Cell Line A-431 Homo sapiens IC50 = 700.0 nM PMID[515949]
NPT762 Cell Line A-431 Homo sapiens IC50 = 500.0 nM PMID[515949]
NPT1171 Cell Line HEp-2 Homo sapiens IC50 = 800.0 nM PMID[515949]
NPT1171 Cell Line HEp-2 Homo sapiens IC50 = 700.0 nM PMID[515949]
NPT1171 Cell Line HEp-2 Homo sapiens IC50 = 600.0 nM PMID[515949]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 500.0 nM PMID[515949]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 300.0 nM PMID[515949]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 400.0 nM PMID[515949]
NPT377 Cell Line OVCAR-3 Homo sapiens IC50 = 900.0 nM PMID[515949]
NPT377 Cell Line OVCAR-3 Homo sapiens IC50 = 1000.0 nM PMID[515949]
NPT2014 Cell Line SW872 Homo sapiens IC50 = 1500.0 nM PMID[515949]
NPT2014 Cell Line SW872 Homo sapiens IC50 = 1400.0 nM PMID[515949]
NPT133 Cell Line ZR-75-1 Homo sapiens IC50 = 300.0 nM PMID[515949]
NPT133 Cell Line ZR-75-1 Homo sapiens IC50 = 500.0 nM PMID[515949]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 100.0 nM PMID[515949]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1300.0 nM PMID[515949]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 900.0 nM PMID[515949]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 400.0 nM PMID[515949]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 700.0 nM PMID[515949]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 70.0 nM PMID[515949]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 60.0 % PMID[515949]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC100 = 2.0 uM PMID[515949]

☑ 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 NPC475309 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
0.8621 High Similarity NPC13710
0.8559 High Similarity NPC473228
0.8559 High Similarity NPC470829
0.8378 Intermediate Similarity NPC100487
0.8198 Intermediate Similarity NPC313569
0.8108 Intermediate Similarity NPC476611
0.8091 Intermediate Similarity NPC187761
0.8091 Intermediate Similarity NPC255592
0.8091 Intermediate Similarity NPC308567
0.8091 Intermediate Similarity NPC261377
0.8091 Intermediate Similarity NPC472015
0.8091 Intermediate Similarity NPC83895
0.8087 Intermediate Similarity NPC315836
0.8087 Intermediate Similarity NPC313668
0.807 Intermediate Similarity NPC254538
0.807 Intermediate Similarity NPC474285
0.8 Intermediate Similarity NPC475960
0.8 Intermediate Similarity NPC476613
0.8 Intermediate Similarity NPC476612
0.8 Intermediate Similarity NPC40812
0.7826 Intermediate Similarity NPC476740
0.7826 Intermediate Similarity NPC476738
0.7807 Intermediate Similarity NPC309398
0.7798 Intermediate Similarity NPC472196
0.7798 Intermediate Similarity NPC320089
0.7798 Intermediate Similarity NPC238090
0.7798 Intermediate Similarity NPC472195
0.7797 Intermediate Similarity NPC287311
0.7778 Intermediate Similarity NPC77337
0.7778 Intermediate Similarity NPC298841
0.776 Intermediate Similarity NPC318135
0.7759 Intermediate Similarity NPC26617
0.7739 Intermediate Similarity NPC86095
0.7739 Intermediate Similarity NPC474917
0.7727 Intermediate Similarity NPC472198
0.7727 Intermediate Similarity NPC71589
0.7727 Intermediate Similarity NPC159698
0.7724 Intermediate Similarity NPC48692
0.7719 Intermediate Similarity NPC13171
0.7719 Intermediate Similarity NPC195510
0.7717 Intermediate Similarity NPC311534
0.7712 Intermediate Similarity NPC477103
0.7712 Intermediate Similarity NPC257240
0.7706 Intermediate Similarity NPC472199
0.7692 Intermediate Similarity NPC177524
0.7692 Intermediate Similarity NPC219900
0.7692 Intermediate Similarity NPC193765
0.7692 Intermediate Similarity NPC392
0.7686 Intermediate Similarity NPC277583
0.7679 Intermediate Similarity NPC472290
0.7674 Intermediate Similarity NPC472769
0.7672 Intermediate Similarity NPC472749
0.7672 Intermediate Similarity NPC472751
0.7672 Intermediate Similarity NPC223450
0.7672 Intermediate Similarity NPC243998
0.7658 Intermediate Similarity NPC36954
0.7656 Intermediate Similarity NPC472770
0.7652 Intermediate Similarity NPC472755
0.7652 Intermediate Similarity NPC284929
0.7652 Intermediate Similarity NPC118761
0.7652 Intermediate Similarity NPC474581
0.7652 Intermediate Similarity NPC37240
0.7652 Intermediate Similarity NPC475367
0.7652 Intermediate Similarity NPC234304
0.7652 Intermediate Similarity NPC267869
0.7652 Intermediate Similarity NPC473816
0.7652 Intermediate Similarity NPC110989
0.7652 Intermediate Similarity NPC197541
0.7638 Intermediate Similarity NPC469757
0.7638 Intermediate Similarity NPC329784
0.7638 Intermediate Similarity NPC146456
0.7638 Intermediate Similarity NPC240070
0.7638 Intermediate Similarity NPC117702
0.7638 Intermediate Similarity NPC42399
0.7638 Intermediate Similarity NPC471357
0.7627 Intermediate Similarity NPC477102
0.7623 Intermediate Similarity NPC471145
0.7623 Intermediate Similarity NPC474483
0.7619 Intermediate Similarity NPC86346
0.7619 Intermediate Similarity NPC75856
0.7619 Intermediate Similarity NPC469379
0.7615 Intermediate Similarity NPC116075
0.7615 Intermediate Similarity NPC469749
0.7615 Intermediate Similarity NPC146857
0.7615 Intermediate Similarity NPC32793
0.7615 Intermediate Similarity NPC247190
0.7603 Intermediate Similarity NPC138303
0.7603 Intermediate Similarity NPC67290
0.7603 Intermediate Similarity NPC133677
0.7603 Intermediate Similarity NPC181145
0.7597 Intermediate Similarity NPC173347
0.7586 Intermediate Similarity NPC472748
0.7586 Intermediate Similarity NPC469869
0.7586 Intermediate Similarity NPC203659
0.7581 Intermediate Similarity NPC476150
0.7581 Intermediate Similarity NPC476127
0.7578 Intermediate Similarity NPC245094
0.7568 Intermediate Similarity NPC475927
0.7568 Intermediate Similarity NPC475832
0.7565 Intermediate Similarity NPC80144
0.7565 Intermediate Similarity NPC177013
0.7565 Intermediate Similarity NPC4899
0.7565 Intermediate Similarity NPC474730
0.7565 Intermediate Similarity NPC35185
0.7565 Intermediate Similarity NPC225353
0.7565 Intermediate Similarity NPC222062
0.7563 Intermediate Similarity NPC83005
0.7559 Intermediate Similarity NPC222307
0.7557 Intermediate Similarity NPC471234
0.7557 Intermediate Similarity NPC329636
0.7545 Intermediate Similarity NPC470379
0.7545 Intermediate Similarity NPC470373
0.7545 Intermediate Similarity NPC472197
0.7544 Intermediate Similarity NPC306344
0.7544 Intermediate Similarity NPC22149
0.7544 Intermediate Similarity NPC255677
0.7544 Intermediate Similarity NPC280963
0.7542 Intermediate Similarity NPC110701
0.7542 Intermediate Similarity NPC473807
0.7542 Intermediate Similarity NPC308191
0.754 Intermediate Similarity NPC469382
0.754 Intermediate Similarity NPC472768
0.754 Intermediate Similarity NPC27363
0.7538 Intermediate Similarity NPC475139
0.7538 Intermediate Similarity NPC180902
0.7522 Intermediate Similarity NPC266842
0.7521 Intermediate Similarity NPC75167
0.7521 Intermediate Similarity NPC106395
0.7521 Intermediate Similarity NPC311592
0.7521 Intermediate Similarity NPC46269
0.752 Intermediate Similarity NPC170880
0.752 Intermediate Similarity NPC476204
0.752 Intermediate Similarity NPC183353
0.752 Intermediate Similarity NPC170084
0.752 Intermediate Similarity NPC202051
0.752 Intermediate Similarity NPC469812
0.7519 Intermediate Similarity NPC469752
0.7519 Intermediate Similarity NPC469754
0.7519 Intermediate Similarity NPC188234
0.7519 Intermediate Similarity NPC329986
0.7519 Intermediate Similarity NPC219085
0.7519 Intermediate Similarity NPC17896
0.7519 Intermediate Similarity NPC469751
0.7519 Intermediate Similarity NPC70542
0.7519 Intermediate Similarity NPC140092
0.7519 Intermediate Similarity NPC471352
0.7519 Intermediate Similarity NPC232785
0.7519 Intermediate Similarity NPC180079
0.7519 Intermediate Similarity NPC125077
0.7519 Intermediate Similarity NPC284406
0.7519 Intermediate Similarity NPC10823
0.7519 Intermediate Similarity NPC89514
0.7519 Intermediate Similarity NPC251866
0.7519 Intermediate Similarity NPC471358
0.7519 Intermediate Similarity NPC197707
0.7519 Intermediate Similarity NPC471360
0.7519 Intermediate Similarity NPC469755
0.7519 Intermediate Similarity NPC86159
0.7519 Intermediate Similarity NPC471361
0.7519 Intermediate Similarity NPC471359
0.7519 Intermediate Similarity NPC469753
0.7519 Intermediate Similarity NPC276838
0.7519 Intermediate Similarity NPC9499
0.7519 Intermediate Similarity NPC6108
0.75 Intermediate Similarity NPC475871
0.75 Intermediate Similarity NPC472750
0.75 Intermediate Similarity NPC194716
0.75 Intermediate Similarity NPC475945
0.75 Intermediate Similarity NPC472747
0.75 Intermediate Similarity NPC11732
0.7481 Intermediate Similarity NPC316915
0.748 Intermediate Similarity NPC471146
0.748 Intermediate Similarity NPC144625
0.7478 Intermediate Similarity NPC28304
0.7478 Intermediate Similarity NPC298255
0.7478 Intermediate Similarity NPC287539
0.7478 Intermediate Similarity NPC67296
0.7478 Intermediate Similarity NPC150923
0.7478 Intermediate Similarity NPC3488
0.7477 Intermediate Similarity NPC476300
0.7477 Intermediate Similarity NPC475912
0.7462 Intermediate Similarity NPC213634
0.7462 Intermediate Similarity NPC469351
0.7458 Intermediate Similarity NPC148270
0.7458 Intermediate Similarity NPC197813
0.7458 Intermediate Similarity NPC80338
0.7456 Intermediate Similarity NPC187268
0.7455 Intermediate Similarity NPC474761
0.7455 Intermediate Similarity NPC476004
0.7444 Intermediate Similarity NPC329675
0.7444 Intermediate Similarity NPC59288
0.7442 Intermediate Similarity NPC270109
0.7442 Intermediate Similarity NPC172823
0.744 Intermediate Similarity NPC470312
0.7438 Intermediate Similarity NPC123855
0.7438 Intermediate Similarity NPC174836
0.7438 Intermediate Similarity NPC76550
0.7438 Intermediate Similarity NPC138757
0.7434 Intermediate Similarity NPC475593
0.7434 Intermediate Similarity NPC475375

  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 NPC475309 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
0.7759 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD6371 Approved
0.7692 Intermediate Similarity NPD6686 Approved
0.752 Intermediate Similarity NPD8513 Phase 3
0.752 Intermediate Similarity NPD8516 Approved
0.752 Intermediate Similarity NPD8515 Approved
0.752 Intermediate Similarity NPD8517 Approved
0.7519 Intermediate Similarity NPD7319 Approved
0.7456 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD7507 Approved
0.7355 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6698 Approved
0.7297 Intermediate Similarity NPD46 Approved
0.7266 Intermediate Similarity NPD7829 Approved
0.7266 Intermediate Similarity NPD7830 Approved
0.7232 Intermediate Similarity NPD7983 Approved
0.7045 Intermediate Similarity NPD7736 Approved
0.7031 Intermediate Similarity NPD8377 Approved
0.7031 Intermediate Similarity NPD8294 Approved
0.7025 Intermediate Similarity NPD6412 Phase 2
0.7023 Intermediate Similarity NPD8451 Approved
0.7 Intermediate Similarity NPD8328 Phase 3
0.7 Intermediate Similarity NPD7642 Approved
0.6977 Remote Similarity NPD8296 Approved
0.6977 Remote Similarity NPD8380 Approved
0.6977 Remote Similarity NPD8379 Approved
0.6977 Remote Similarity NPD8335 Approved
0.6977 Remote Similarity NPD8378 Approved
0.6977 Remote Similarity NPD8033 Approved
0.697 Remote Similarity NPD8448 Approved
0.697 Remote Similarity NPD8293 Discontinued
0.697 Remote Similarity NPD8074 Phase 3
0.6947 Remote Similarity NPD8340 Approved
0.6947 Remote Similarity NPD8299 Approved
0.6947 Remote Similarity NPD8342 Approved
0.6947 Remote Similarity NPD8341 Approved
0.6923 Remote Similarity NPD8080 Discontinued
0.6923 Remote Similarity NPD6370 Approved
0.6897 Remote Similarity NPD1698 Clinical (unspecified phase)
0.688 Remote Similarity NPD6053 Discontinued
0.6875 Remote Similarity NPD7328 Approved
0.6875 Remote Similarity NPD7327 Approved
0.6846 Remote Similarity NPD8444 Approved
0.6842 Remote Similarity NPD7838 Discovery
0.6838 Remote Similarity NPD7839 Suspended
0.6822 Remote Similarity NPD7516 Approved
0.6818 Remote Similarity NPD7492 Approved
0.6815 Remote Similarity NPD8390 Approved
0.6815 Remote Similarity NPD8392 Approved
0.6815 Remote Similarity NPD8391 Approved
0.6797 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6769 Remote Similarity NPD6054 Approved
0.6767 Remote Similarity NPD6616 Approved
0.6763 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6718 Remote Similarity NPD7503 Approved
0.6718 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6716 Remote Similarity NPD7078 Approved
0.6693 Remote Similarity NPD8133 Approved
0.6667 Remote Similarity NPD8337 Approved
0.6667 Remote Similarity NPD8336 Approved
0.6641 Remote Similarity NPD6059 Approved
0.6641 Remote Similarity NPD6319 Approved
0.6615 Remote Similarity NPD7641 Discontinued
0.6591 Remote Similarity NPD6015 Approved
0.6591 Remote Similarity NPD6016 Approved
0.6581 Remote Similarity NPD5779 Approved
0.6581 Remote Similarity NPD5778 Approved
0.6552 Remote Similarity NPD5785 Approved
0.6541 Remote Similarity NPD5988 Approved
0.6538 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6538 Remote Similarity NPD7115 Discovery
0.6484 Remote Similarity NPD6882 Approved
0.6484 Remote Similarity NPD8297 Approved
0.6466 Remote Similarity NPD8267 Approved
0.6466 Remote Similarity NPD8269 Approved
0.6466 Remote Similarity NPD8266 Approved
0.6466 Remote Similarity NPD8268 Approved
0.6454 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6446 Remote Similarity NPD4225 Approved
0.6412 Remote Similarity NPD6009 Approved
0.6404 Remote Similarity NPD5363 Approved
0.6387 Remote Similarity NPD5282 Discontinued
0.6378 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6357 Remote Similarity NPD8338 Approved
0.6348 Remote Similarity NPD5786 Approved
0.6341 Remote Similarity NPD5344 Discontinued
0.6325 Remote Similarity NPD1695 Approved
0.6308 Remote Similarity NPD4632 Approved
0.6299 Remote Similarity NPD5345 Clinical (unspecified phase)
0.629 Remote Similarity NPD8139 Approved
0.629 Remote Similarity NPD8086 Approved
0.629 Remote Similarity NPD8084 Approved
0.629 Remote Similarity NPD8085 Approved
0.629 Remote Similarity NPD8082 Approved
0.629 Remote Similarity NPD8083 Approved
0.629 Remote Similarity NPD8138 Approved
0.6283 Remote Similarity NPD6435 Approved
0.6277 Remote Similarity NPD8273 Phase 1
0.6268 Remote Similarity NPD8415 Approved
0.6261 Remote Similarity NPD1733 Clinical (unspecified phase)
0.626 Remote Similarity NPD7640 Approved
0.626 Remote Similarity NPD7639 Approved
0.624 Remote Similarity NPD8275 Approved
0.624 Remote Similarity NPD8276 Approved
0.6228 Remote Similarity NPD5362 Discontinued
0.6228 Remote Similarity NPD7154 Phase 3
0.619 Remote Similarity NPD8081 Approved
0.6187 Remote Similarity NPD6033 Approved
0.6186 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6186 Remote Similarity NPD6101 Approved
0.6179 Remote Similarity NPD7638 Approved
0.6174 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6172 Remote Similarity NPD7320 Approved
0.6172 Remote Similarity NPD6899 Approved
0.6172 Remote Similarity NPD6881 Approved
0.6154 Remote Similarity NPD6650 Approved
0.6154 Remote Similarity NPD4250 Approved
0.6154 Remote Similarity NPD4251 Approved
0.6154 Remote Similarity NPD8130 Phase 1
0.6154 Remote Similarity NPD6649 Approved
0.6142 Remote Similarity NPD8393 Approved
0.6142 Remote Similarity NPD5739 Approved
0.6142 Remote Similarity NPD6402 Approved
0.6142 Remote Similarity NPD7128 Approved
0.6142 Remote Similarity NPD6675 Approved
0.614 Remote Similarity NPD4270 Approved
0.614 Remote Similarity NPD4269 Approved
0.6124 Remote Similarity NPD6373 Approved
0.6124 Remote Similarity NPD6372 Approved
0.6124 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6106 Remote Similarity NPD5368 Approved
0.6094 Remote Similarity NPD5697 Approved
0.6083 Remote Similarity NPD6411 Approved
0.6078 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6077 Remote Similarity NPD6883 Approved
0.6077 Remote Similarity NPD4634 Approved
0.6077 Remote Similarity NPD7290 Approved
0.6077 Remote Similarity NPD7102 Approved
0.6068 Remote Similarity NPD4249 Approved
0.6063 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6056 Remote Similarity NPD7260 Phase 2
0.6053 Remote Similarity NPD5369 Approved
0.6045 Remote Similarity NPD7500 Approved
0.6031 Remote Similarity NPD6847 Approved
0.6031 Remote Similarity NPD6617 Approved
0.6031 Remote Similarity NPD6869 Approved
0.6014 Remote Similarity NPD7604 Phase 2
0.6014 Remote Similarity NPD6067 Discontinued
0.6 Remote Similarity NPD6014 Approved
0.6 Remote Similarity NPD6648 Approved
0.6 Remote Similarity NPD6013 Approved
0.6 Remote Similarity NPD6012 Approved
0.5986 Remote Similarity NPD5956 Approved
0.5985 Remote Similarity NPD5983 Phase 2
0.5983 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5969 Remote Similarity NPD8140 Approved
0.5969 Remote Similarity NPD5701 Approved
0.5969 Remote Similarity NPD8307 Discontinued
0.5968 Remote Similarity NPD6083 Phase 2
0.5968 Remote Similarity NPD6084 Phase 2
0.5965 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5965 Remote Similarity NPD4821 Approved
0.5965 Remote Similarity NPD4252 Approved
0.5965 Remote Similarity NPD4820 Approved
0.5965 Remote Similarity NPD4822 Approved
0.5965 Remote Similarity NPD4819 Approved
0.5954 Remote Similarity NPD5955 Clinical (unspecified phase)
0.595 Remote Similarity NPD7637 Suspended
0.5929 Remote Similarity NPD6336 Discontinued
0.5923 Remote Similarity NPD6011 Approved
0.5906 Remote Similarity NPD5211 Phase 2
0.5906 Remote Similarity NPD8384 Approved
0.5903 Remote Similarity NPD6845 Suspended
0.5891 Remote Similarity NPD6008 Approved
0.5878 Remote Similarity NPD8305 Approved
0.5878 Remote Similarity NPD8306 Approved
0.5874 Remote Similarity NPD6914 Discontinued
0.587 Remote Similarity NPD6921 Approved
0.5868 Remote Similarity NPD7799 Discontinued
0.5862 Remote Similarity NPD5209 Approved
0.5862 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5833 Remote Similarity NPD8087 Discontinued
0.5814 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5814 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5814 Remote Similarity NPD5141 Approved
0.5812 Remote Similarity NPD6110 Phase 1
0.5806 Remote Similarity NPD5695 Phase 3
0.5789 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4271 Approved
0.5789 Remote Similarity NPD4268 Approved
0.5789 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5781 Remote Similarity NPD7632 Discontinued
0.5748 Remote Similarity NPD5285 Approved
0.5748 Remote Similarity NPD4696 Approved
0.5748 Remote Similarity NPD5286 Approved
0.5735 Remote Similarity NPD6274 Approved
0.5726 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5725 Remote Similarity NPD7101 Approved
0.5725 Remote Similarity NPD5954 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