Structure

Physi-Chem Properties

Molecular Weight:  464.29
Volume:  515.836
LogP:  4.055
LogD:  3.742
LogS:  -5.033
# Rotatable Bonds:  5
TPSA:  71.44
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.359
Synthetic Accessibility Score:  4.616
Fsp3:  0.567
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.301
MDCK Permeability:  2.3760232579661533e-05
Pgp-inhibitor:  0.552
Pgp-substrate:  0.258
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.277
Plasma Protein Binding (PPB):  95.07029724121094%
Volume Distribution (VD):  0.653
Pgp-substrate:  5.0398640632629395%

ADMET: Metabolism

CYP1A2-inhibitor:  0.179
CYP1A2-substrate:  0.927
CYP2C19-inhibitor:  0.289
CYP2C19-substrate:  0.779
CYP2C9-inhibitor:  0.602
CYP2C9-substrate:  0.979
CYP2D6-inhibitor:  0.806
CYP2D6-substrate:  0.875
CYP3A4-inhibitor:  0.652
CYP3A4-substrate:  0.338

ADMET: Excretion

Clearance (CL):  1.396
Half-life (T1/2):  0.698

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.364
Drug-inuced Liver Injury (DILI):  0.287
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.713
Maximum Recommended Daily Dose:  0.935
Skin Sensitization:  0.833
Carcinogencity:  0.72
Eye Corrosion:  0.003
Eye Irritation:  0.024
Respiratory Toxicity:  0.96

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

  Natural Product: NPC3856

Natural Product ID:  NPC3856
Common Name*:   Stelletin E
IUPAC Name:   (2E,4E,6E,8E,10Z)-10-[(3aS,5aR,9aR,9bS)-3a,6,6,9a-tetramethyl-2,7-dioxo-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoic acid
Synonyms:   (-)-Stellettin E
Standard InCHIKey:  IIPLLKSCMYHUOP-HJMNRKRYSA-N
Standard InCHI:  InChI=1S/C30H40O4/c1-19(11-9-13-21(3)27(33)34)10-8-12-20(2)26-22(31)18-24-29(6)17-15-25(32)28(4,5)23(29)14-16-30(24,26)7/h8-13,23-24H,14-18H2,1-7H3,(H,33,34)/b11-9+,12-8+,19-10+,21-13+,26-20+/t23-,24-,29-,30-/m0/s1
SMILES:  C/C(=CC=CC(=C1/C(=O)C[C@H]2[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@]12C)C)/C=C/C=C(C)/C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL490363
PubChem CID:   6519634
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[11858759]
NPO32624 rhabdastrella aff. distincta Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[15620246]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[16499318]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[16562838]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[17524651]
NPO32624 rhabdastrella aff. distincta Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[18826276]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[20627740]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[20718449]
NPO28502 Rhabdastrella globostellata Species Ancorinidae 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
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 4570.0 nM PMID[502430]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 39.0 nM PMID[502430]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 5390.0 nM PMID[502430]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 5.0 ug.mL-1 PMID[502431]
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 5.0 ug.mL-1 PMID[502431]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 5.0 ug.mL-1 PMID[502431]
NPT165 Cell Line HeLa Homo sapiens IC50 > 5.0 ug.mL-1 PMID[502431]
NPT179 Cell Line A2780 Homo sapiens IC50 < 500.0 nM PMID[502432]
NPT81 Cell Line A549 Homo sapiens IC50 = 18610.0 nM PMID[502432]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 13700.0 nM PMID[502432]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 50000.0 nM PMID[502432]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 5.0 ug.mL-1 PMID[502431]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 50000.0 nM PMID[502432]

☑ 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 NPC3856 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 NPC279639
0.987 High Similarity NPC469805
0.987 High Similarity NPC469804
0.987 High Similarity NPC469799
0.987 High Similarity NPC469806
0.961 High Similarity NPC469797
0.961 High Similarity NPC469798
0.9268 High Similarity NPC476293
0.9136 High Similarity NPC87552
0.9125 High Similarity NPC472239
0.9059 High Similarity NPC474018
0.9059 High Similarity NPC473986
0.9024 High Similarity NPC60350
0.9012 High Similarity NPC474790
0.9012 High Similarity NPC474976
0.8961 High Similarity NPC469803
0.8902 High Similarity NPC181743
0.8902 High Similarity NPC178025
0.8902 High Similarity NPC16287
0.8889 High Similarity NPC472867
0.8889 High Similarity NPC3511
0.8889 High Similarity NPC142253
0.8831 High Similarity NPC474796
0.8831 High Similarity NPC329866
0.8831 High Similarity NPC474797
0.8795 High Similarity NPC8571
0.8718 High Similarity NPC476346
0.8652 High Similarity NPC250757
0.8652 High Similarity NPC301534
0.8621 High Similarity NPC204341
0.8605 High Similarity NPC262043
0.8588 High Similarity NPC75315
0.8588 High Similarity NPC163016
0.8588 High Similarity NPC236618
0.8571 High Similarity NPC133253
0.8571 High Similarity NPC21944
0.8554 High Similarity NPC97913
0.8488 Intermediate Similarity NPC117122
0.8471 Intermediate Similarity NPC186975
0.8471 Intermediate Similarity NPC472869
0.8462 Intermediate Similarity NPC180015
0.8462 Intermediate Similarity NPC130016
0.8462 Intermediate Similarity NPC109576
0.8462 Intermediate Similarity NPC56747
0.8452 Intermediate Similarity NPC19849
0.8452 Intermediate Similarity NPC164577
0.8452 Intermediate Similarity NPC472864
0.8409 Intermediate Similarity NPC23217
0.8391 Intermediate Similarity NPC66344
0.8391 Intermediate Similarity NPC474844
0.8372 Intermediate Similarity NPC136948
0.8353 Intermediate Similarity NPC269638
0.8353 Intermediate Similarity NPC29447
0.828 Intermediate Similarity NPC282524
0.8276 Intermediate Similarity NPC472870
0.8272 Intermediate Similarity NPC91665
0.8261 Intermediate Similarity NPC108368
0.8261 Intermediate Similarity NPC57079
0.8235 Intermediate Similarity NPC248758
0.8235 Intermediate Similarity NPC472865
0.8222 Intermediate Similarity NPC299100
0.8214 Intermediate Similarity NPC320514
0.8172 Intermediate Similarity NPC266955
0.8171 Intermediate Similarity NPC198240
0.8161 Intermediate Similarity NPC128644
0.8148 Intermediate Similarity NPC469796
0.8148 Intermediate Similarity NPC469793
0.8132 Intermediate Similarity NPC476174
0.8132 Intermediate Similarity NPC180950
0.8132 Intermediate Similarity NPC171395
0.8105 Intermediate Similarity NPC72151
0.8101 Intermediate Similarity NPC54123
0.8095 Intermediate Similarity NPC477372
0.8095 Intermediate Similarity NPC4166
0.8095 Intermediate Similarity NPC278459
0.809 Intermediate Similarity NPC472866
0.8085 Intermediate Similarity NPC115899
0.8068 Intermediate Similarity NPC72397
0.8065 Intermediate Similarity NPC235464
0.8065 Intermediate Similarity NPC166745
0.8049 Intermediate Similarity NPC61952
0.8043 Intermediate Similarity NPC29152
0.8025 Intermediate Similarity NPC473171
0.8022 Intermediate Similarity NPC474690
0.8 Intermediate Similarity NPC251705
0.8 Intermediate Similarity NPC303613
0.8 Intermediate Similarity NPC311092
0.8 Intermediate Similarity NPC474228
0.8 Intermediate Similarity NPC470113
0.8 Intermediate Similarity NPC320447
0.8 Intermediate Similarity NPC94200
0.7978 Intermediate Similarity NPC118011
0.7978 Intermediate Similarity NPC36668
0.7975 Intermediate Similarity NPC251929
0.7975 Intermediate Similarity NPC2634
0.7975 Intermediate Similarity NPC265782
0.7957 Intermediate Similarity NPC156546
0.7955 Intermediate Similarity NPC476409
0.7935 Intermediate Similarity NPC88310
0.7935 Intermediate Similarity NPC293052
0.7931 Intermediate Similarity NPC11711
0.7931 Intermediate Similarity NPC472940
0.7931 Intermediate Similarity NPC472931
0.7927 Intermediate Similarity NPC19907
0.7927 Intermediate Similarity NPC180886
0.7927 Intermediate Similarity NPC69408
0.7917 Intermediate Similarity NPC475050
0.7912 Intermediate Similarity NPC472871
0.7912 Intermediate Similarity NPC469939
0.7912 Intermediate Similarity NPC242069
0.7907 Intermediate Similarity NPC168188
0.7907 Intermediate Similarity NPC49019
0.7907 Intermediate Similarity NPC69279
0.7907 Intermediate Similarity NPC83569
0.7907 Intermediate Similarity NPC310470
0.7907 Intermediate Similarity NPC118423
0.7907 Intermediate Similarity NPC470015
0.7907 Intermediate Similarity NPC41539
0.7901 Intermediate Similarity NPC309852
0.7901 Intermediate Similarity NPC20025
0.7895 Intermediate Similarity NPC99411
0.7889 Intermediate Similarity NPC474842
0.7889 Intermediate Similarity NPC475965
0.7882 Intermediate Similarity NPC147066
0.7875 Intermediate Similarity NPC305501
0.7875 Intermediate Similarity NPC234707
0.7875 Intermediate Similarity NPC115023
0.7875 Intermediate Similarity NPC470078
0.7865 Intermediate Similarity NPC48107
0.7857 Intermediate Similarity NPC190211
0.7857 Intermediate Similarity NPC477371
0.7849 Intermediate Similarity NPC471153
0.7849 Intermediate Similarity NPC472941
0.7849 Intermediate Similarity NPC456
0.7848 Intermediate Similarity NPC139397
0.7841 Intermediate Similarity NPC6247
0.7841 Intermediate Similarity NPC168248
0.7831 Intermediate Similarity NPC97377
0.7812 Intermediate Similarity NPC32577
0.7812 Intermediate Similarity NPC114540
0.7812 Intermediate Similarity NPC155332
0.7805 Intermediate Similarity NPC293803
0.7805 Intermediate Similarity NPC65650
0.7805 Intermediate Similarity NPC476844
0.7805 Intermediate Similarity NPC255650
0.7802 Intermediate Similarity NPC476187
0.7792 Intermediate Similarity NPC107258
0.7791 Intermediate Similarity NPC133391
0.7791 Intermediate Similarity NPC268122
0.7789 Intermediate Similarity NPC35751
0.7778 Intermediate Similarity NPC470045
0.7778 Intermediate Similarity NPC214387
0.7778 Intermediate Similarity NPC470044
0.7766 Intermediate Similarity NPC474785
0.7766 Intermediate Similarity NPC253826
0.7766 Intermediate Similarity NPC474938
0.7755 Intermediate Similarity NPC266570
0.7755 Intermediate Similarity NPC189863
0.7753 Intermediate Similarity NPC141292
0.775 Intermediate Similarity NPC35734
0.775 Intermediate Similarity NPC282593
0.775 Intermediate Similarity NPC159577
0.775 Intermediate Similarity NPC307176
0.775 Intermediate Similarity NPC260040
0.7742 Intermediate Similarity NPC209355
0.7738 Intermediate Similarity NPC105197
0.7738 Intermediate Similarity NPC169095
0.7738 Intermediate Similarity NPC74410
0.7738 Intermediate Similarity NPC275494
0.7738 Intermediate Similarity NPC82635
0.7738 Intermediate Similarity NPC471409
0.7738 Intermediate Similarity NPC179028
0.7732 Intermediate Similarity NPC329345
0.7732 Intermediate Similarity NPC473283
0.7732 Intermediate Similarity NPC475526
0.7727 Intermediate Similarity NPC123319
0.7727 Intermediate Similarity NPC94531
0.7727 Intermediate Similarity NPC474537
0.7727 Intermediate Similarity NPC142649
0.7727 Intermediate Similarity NPC311702
0.7717 Intermediate Similarity NPC474736
0.7711 Intermediate Similarity NPC474463
0.7708 Intermediate Similarity NPC476223
0.7708 Intermediate Similarity NPC476240
0.7708 Intermediate Similarity NPC224720
0.7708 Intermediate Similarity NPC118174
0.7701 Intermediate Similarity NPC472740
0.7701 Intermediate Similarity NPC102197
0.7701 Intermediate Similarity NPC167103
0.7701 Intermediate Similarity NPC477373
0.7692 Intermediate Similarity NPC242945
0.7692 Intermediate Similarity NPC259156
0.7692 Intermediate Similarity NPC477147
0.7692 Intermediate Similarity NPC81907
0.7692 Intermediate Similarity NPC255781
0.7692 Intermediate Similarity NPC477149
0.7684 Intermediate Similarity NPC471717
0.7684 Intermediate Similarity NPC197386
0.7684 Intermediate Similarity NPC98868
0.7684 Intermediate Similarity NPC103051

  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 NPC3856 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
0.8354 Intermediate Similarity NPD4058 Approved
0.7975 Intermediate Similarity NPD4691 Approved
0.7901 Intermediate Similarity NPD5733 Approved
0.7901 Intermediate Similarity NPD4687 Approved
0.7848 Intermediate Similarity NPD4137 Phase 3
0.7802 Intermediate Similarity NPD5281 Approved
0.7802 Intermediate Similarity NPD5284 Approved
0.775 Intermediate Similarity NPD4747 Approved
0.7654 Intermediate Similarity NPD5276 Approved
0.7529 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD4623 Approved
0.7444 Intermediate Similarity NPD4519 Discontinued
0.7423 Intermediate Similarity NPD6404 Discontinued
0.7391 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4221 Approved
0.7386 Intermediate Similarity NPD4223 Phase 3
0.7333 Intermediate Similarity NPD5329 Approved
0.7303 Intermediate Similarity NPD3527 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD6672 Approved
0.7283 Intermediate Similarity NPD5737 Approved
0.7253 Intermediate Similarity NPD4694 Approved
0.7253 Intermediate Similarity NPD5690 Phase 2
0.7253 Intermediate Similarity NPD6409 Approved
0.7253 Intermediate Similarity NPD6684 Approved
0.7253 Intermediate Similarity NPD5330 Approved
0.7253 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD7146 Approved
0.7253 Intermediate Similarity NPD7334 Approved
0.7253 Intermediate Similarity NPD5280 Approved
0.7253 Intermediate Similarity NPD7521 Approved
0.7234 Intermediate Similarity NPD7637 Suspended
0.7234 Intermediate Similarity NPD6079 Approved
0.7234 Intermediate Similarity NPD6050 Approved
0.7234 Intermediate Similarity NPD5694 Approved
0.7222 Intermediate Similarity NPD4197 Approved
0.7222 Intermediate Similarity NPD3133 Approved
0.7222 Intermediate Similarity NPD3665 Phase 1
0.7222 Intermediate Similarity NPD3666 Approved
0.7216 Intermediate Similarity NPD6083 Phase 2
0.7216 Intermediate Similarity NPD6084 Phase 2
0.7204 Intermediate Similarity NPD6904 Approved
0.7204 Intermediate Similarity NPD6673 Approved
0.7204 Intermediate Similarity NPD6080 Approved
0.7191 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD4194 Approved
0.7179 Intermediate Similarity NPD4193 Approved
0.7179 Intermediate Similarity NPD4191 Approved
0.7179 Intermediate Similarity NPD4192 Approved
0.7159 Intermediate Similarity NPD4695 Discontinued
0.7158 Intermediate Similarity NPD6399 Phase 3
0.7143 Intermediate Similarity NPD5363 Approved
0.7128 Intermediate Similarity NPD5785 Approved
0.7128 Intermediate Similarity NPD5207 Approved
0.7128 Intermediate Similarity NPD5692 Phase 3
0.7126 Intermediate Similarity NPD3617 Approved
0.7097 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6903 Approved
0.7071 Intermediate Similarity NPD7639 Approved
0.7071 Intermediate Similarity NPD7640 Approved
0.7065 Intermediate Similarity NPD3618 Phase 1
0.7065 Intermediate Similarity NPD4693 Phase 3
0.7065 Intermediate Similarity NPD5279 Phase 3
0.7065 Intermediate Similarity NPD4690 Approved
0.7065 Intermediate Similarity NPD5205 Approved
0.7065 Intermediate Similarity NPD4138 Approved
0.7065 Intermediate Similarity NPD4689 Approved
0.7065 Intermediate Similarity NPD4688 Approved
0.7053 Intermediate Similarity NPD5693 Phase 1
0.7053 Intermediate Similarity NPD7515 Phase 2
0.7045 Intermediate Similarity NPD4195 Approved
0.7033 Intermediate Similarity NPD4786 Approved
0.7021 Intermediate Similarity NPD5328 Approved
0.7021 Intermediate Similarity NPD4753 Phase 2
0.701 Intermediate Similarity NPD5210 Approved
0.701 Intermediate Similarity NPD5695 Phase 3
0.701 Intermediate Similarity NPD4629 Approved
0.7 Intermediate Similarity NPD3667 Approved
0.697 Remote Similarity NPD5696 Approved
0.697 Remote Similarity NPD7638 Approved
0.6939 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6939 Remote Similarity NPD5222 Approved
0.6939 Remote Similarity NPD5221 Approved
0.6931 Remote Similarity NPD5211 Phase 2
0.6923 Remote Similarity NPD6899 Approved
0.6923 Remote Similarity NPD6881 Approved
0.6915 Remote Similarity NPD5208 Approved
0.6907 Remote Similarity NPD7748 Approved
0.6882 Remote Similarity NPD6098 Approved
0.6881 Remote Similarity NPD7115 Discovery
0.6869 Remote Similarity NPD5173 Approved
0.6837 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6827 Remote Similarity NPD5697 Approved
0.6813 Remote Similarity NPD4270 Approved
0.6813 Remote Similarity NPD4269 Approved
0.6809 Remote Similarity NPD3573 Approved
0.6796 Remote Similarity NPD5141 Approved
0.6792 Remote Similarity NPD6883 Approved
0.6792 Remote Similarity NPD7102 Approved
0.6792 Remote Similarity NPD7290 Approved
0.6778 Remote Similarity NPD4252 Approved
0.6771 Remote Similarity NPD4096 Approved
0.6768 Remote Similarity NPD7614 Phase 1
0.6762 Remote Similarity NPD6011 Approved
0.6739 Remote Similarity NPD5362 Discontinued
0.6739 Remote Similarity NPD4788 Approved
0.6737 Remote Similarity NPD4518 Approved
0.6733 Remote Similarity NPD5285 Approved
0.6733 Remote Similarity NPD5286 Approved
0.6733 Remote Similarity NPD4696 Approved
0.6731 Remote Similarity NPD6675 Approved
0.6731 Remote Similarity NPD7128 Approved
0.6731 Remote Similarity NPD6402 Approved
0.6731 Remote Similarity NPD5739 Approved
0.6729 Remote Similarity NPD8130 Phase 1
0.6729 Remote Similarity NPD6869 Approved
0.6729 Remote Similarity NPD6649 Approved
0.6729 Remote Similarity NPD6847 Approved
0.6729 Remote Similarity NPD6617 Approved
0.6729 Remote Similarity NPD6650 Approved
0.67 Remote Similarity NPD7902 Approved
0.6698 Remote Similarity NPD6012 Approved
0.6698 Remote Similarity NPD6013 Approved
0.6698 Remote Similarity NPD6014 Approved
0.6667 Remote Similarity NPD5654 Approved
0.6667 Remote Similarity NPD5223 Approved
0.6667 Remote Similarity NPD8297 Approved
0.6667 Remote Similarity NPD6882 Approved
0.6667 Remote Similarity NPD3668 Phase 3
0.6633 Remote Similarity NPD4202 Approved
0.6633 Remote Similarity NPD5133 Approved
0.6604 Remote Similarity NPD7320 Approved
0.6602 Remote Similarity NPD5091 Approved
0.6602 Remote Similarity NPD5225 Approved
0.6602 Remote Similarity NPD5224 Approved
0.6602 Remote Similarity NPD5226 Approved
0.6602 Remote Similarity NPD4633 Approved
0.66 Remote Similarity NPD4697 Phase 3
0.6596 Remote Similarity NPD1694 Approved
0.6596 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6593 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6593 Remote Similarity NPD7514 Phase 3
0.6566 Remote Similarity NPD5769 Clinical (unspecified phase)
0.6566 Remote Similarity NPD6001 Approved
0.6556 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7145 Approved
0.6542 Remote Similarity NPD6373 Approved
0.6542 Remote Similarity NPD6372 Approved
0.6538 Remote Similarity NPD5174 Approved
0.6538 Remote Similarity NPD5175 Approved
0.6535 Remote Similarity NPD4755 Approved
0.6535 Remote Similarity NPD5959 Approved
0.6526 Remote Similarity NPD5786 Approved
0.6522 Remote Similarity NPD8028 Phase 2
0.6522 Remote Similarity NPD6902 Approved
0.6512 Remote Similarity NPD7143 Approved
0.6512 Remote Similarity NPD7144 Approved
0.6509 Remote Similarity NPD6614 Approved
0.6509 Remote Similarity NPD5701 Approved
0.6486 Remote Similarity NPD6868 Approved
0.6471 Remote Similarity NPD4225 Approved
0.6465 Remote Similarity NPD5779 Approved
0.6465 Remote Similarity NPD5778 Approved
0.6455 Remote Similarity NPD4632 Approved
0.6452 Remote Similarity NPD5209 Approved
0.6449 Remote Similarity NPD6686 Approved
0.6444 Remote Similarity NPD6925 Approved
0.6444 Remote Similarity NPD5776 Phase 2
0.6444 Remote Similarity NPD4756 Discovery
0.6442 Remote Similarity NPD7632 Discontinued
0.6437 Remote Similarity NPD7152 Approved
0.6437 Remote Similarity NPD7150 Approved
0.6437 Remote Similarity NPD6081 Approved
0.6437 Remote Similarity NPD7151 Approved
0.6422 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6421 Remote Similarity NPD1696 Phase 3
0.6413 Remote Similarity NPD7332 Phase 2
0.6413 Remote Similarity NPD4821 Approved
0.6413 Remote Similarity NPD4819 Approved
0.6413 Remote Similarity NPD5368 Approved
0.6413 Remote Similarity NPD4822 Approved
0.6413 Remote Similarity NPD4820 Approved
0.6408 Remote Similarity NPD4700 Approved
0.6404 Remote Similarity NPD8039 Approved
0.64 Remote Similarity NPD7901 Clinical (unspecified phase)
0.64 Remote Similarity NPD7900 Approved
0.6395 Remote Similarity NPD6923 Approved
0.6395 Remote Similarity NPD6922 Approved
0.6383 Remote Similarity NPD5331 Approved
0.6383 Remote Similarity NPD5332 Approved
0.6383 Remote Similarity NPD7154 Phase 3
0.6381 Remote Similarity NPD6052 Approved
0.6375 Remote Similarity NPD287 Approved
0.6374 Remote Similarity NPD4268 Approved
0.6374 Remote Similarity NPD4271 Approved
0.6372 Remote Similarity NPD6335 Approved
0.6364 Remote Similarity NPD8034 Phase 2
0.6364 Remote Similarity NPD8035 Phase 2
0.6364 Remote Similarity NPD6411 Approved
0.6355 Remote Similarity NPD6412 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