Structure

Physi-Chem Properties

Molecular Weight:  594.18
Volume:  571.702
LogP:  3.46
LogD:  0.866
LogS:  -0.913
# Rotatable Bonds:  6
TPSA:  193.96
# H-Bond Aceptor:  13
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.165
Synthetic Accessibility Score:  5.029
Fsp3:  0.333
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.414
MDCK Permeability:  9.407960533280857e-06
Pgp-inhibitor:  0.017
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.675
20% Bioavailability (F20%):  0.404
30% Bioavailability (F30%):  0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.04
Plasma Protein Binding (PPB):  99.15257263183594%
Volume Distribution (VD):  0.623
Pgp-substrate:  1.4813100099563599%

ADMET: Metabolism

CYP1A2-inhibitor:  0.138
CYP1A2-substrate:  0.097
CYP2C19-inhibitor:  0.121
CYP2C19-substrate:  0.094
CYP2C9-inhibitor:  0.856
CYP2C9-substrate:  0.969
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.065
CYP3A4-inhibitor:  0.258
CYP3A4-substrate:  0.92

ADMET: Excretion

Clearance (CL):  2.486
Half-life (T1/2):  0.682

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.835
Drug-inuced Liver Injury (DILI):  0.996
AMES Toxicity:  0.043
Rat Oral Acute Toxicity:  0.728
Maximum Recommended Daily Dose:  0.889
Skin Sensitization:  0.19
Carcinogencity:  0.588
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.197

Download Data

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

  Natural Product: NPC471847

Natural Product ID:  NPC471847
Common Name*:   Episarcoviolin Beta
IUPAC Name:   2-[(5R,11aR)-3-[(2S)-butan-2-yl]-11a-[(2R)-butan-2-yl]-2,4-dihydroxy-5-oxido-1-oxopyrazino[1,2-b][1,4,2]benzodioxazin-5-ium-9-yl]-3,6-dihydroxy-5-(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione
Synonyms:  
Standard InCHIKey:  HEXAABFDZKPMQT-DHJISALFSA-N
Standard InCHI:  InChI=1S/C30H30N2O11/c1-5-14(3)23-28(38)32(41)30(15(4)6-2,29(39)31(23)40)42-20-13-17(9-12-19(20)43-32)22-26(36)24(34)21(25(35)27(22)37)16-7-10-18(33)11-8-16/h7-15,33-34,37-38,40H,5-6H2,1-4H3/t14-,15+,30+,32+/m0/s1
SMILES:  CCC(C)C1=C([N+]2(C(C(=O)N1O)(OC3=C(O2)C=CC(=C3)C4=C(C(=O)C(=C(C4=O)O)C5=CC=C(C=C5)O)O)C(C)CC)[O-])O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3238005
PubChem CID:   90671614
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO26394 Sarcodon leucopus Species Thelephoraceae Eukaryota Fruits n.a. n.a. PMID[10757716]
NPO26394 Sarcodon leucopus Species Thelephoraceae Eukaryota n.a. Tibet, China n.a. PMID[24645629]
NPO26394 Sarcodon leucopus Species Thelephoraceae 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
NPT1 Others Radical scavenging activity IC50 = 12000.0 nM PMID[547540]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 146.0 U PMID[547540]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 17000.0 nM PMID[547540]
NPT625 Tissue Liver Mus musculus IC50 = 27000.0 nM PMID[547540]
NPT2 Others Unspecified IC50 = 1070.0 nM PMID[547540]

☑ 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 NPC471847 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 NPC18633
0.8245 Intermediate Similarity NPC119291
0.8245 Intermediate Similarity NPC471849
0.8245 Intermediate Similarity NPC161144
0.8245 Intermediate Similarity NPC471848
0.7079 Intermediate Similarity NPC474556
0.7 Intermediate Similarity NPC32064
0.7 Intermediate Similarity NPC475718
0.6968 Remote Similarity NPC164608
0.6943 Remote Similarity NPC138083
0.6908 Remote Similarity NPC92235
0.6842 Remote Similarity NPC239302
0.6837 Remote Similarity NPC234069
0.6824 Remote Similarity NPC172673
0.6821 Remote Similarity NPC276120
0.6802 Remote Similarity NPC64140
0.6802 Remote Similarity NPC174122
0.68 Remote Similarity NPC284409
0.6746 Remote Similarity NPC471532
0.6735 Remote Similarity NPC475566
0.6731 Remote Similarity NPC471561
0.6723 Remote Similarity NPC138438
0.6723 Remote Similarity NPC908
0.6717 Remote Similarity NPC29531
0.6698 Remote Similarity NPC471531
0.6685 Remote Similarity NPC236769
0.6685 Remote Similarity NPC153644
0.6685 Remote Similarity NPC76376
0.6684 Remote Similarity NPC158900
0.6648 Remote Similarity NPC469540
0.6648 Remote Similarity NPC98009
0.6648 Remote Similarity NPC469539
0.6647 Remote Similarity NPC132308
0.6633 Remote Similarity NPC298339
0.6631 Remote Similarity NPC288353
0.6631 Remote Similarity NPC178854
0.663 Remote Similarity NPC50728
0.663 Remote Similarity NPC219330
0.663 Remote Similarity NPC166753
0.6615 Remote Similarity NPC329816
0.6613 Remote Similarity NPC236223
0.6613 Remote Similarity NPC58382
0.6613 Remote Similarity NPC179126
0.6613 Remote Similarity NPC162351
0.6613 Remote Similarity NPC270620
0.6613 Remote Similarity NPC246204
0.6613 Remote Similarity NPC78326
0.6612 Remote Similarity NPC478189
0.6611 Remote Similarity NPC9373
0.6608 Remote Similarity NPC226661
0.6596 Remote Similarity NPC183
0.6588 Remote Similarity NPC90128
0.6588 Remote Similarity NPC84076
0.6588 Remote Similarity NPC303680
0.6584 Remote Similarity NPC471563
0.6578 Remote Similarity NPC32557
0.6578 Remote Similarity NPC189960
0.6576 Remote Similarity NPC159103
0.6573 Remote Similarity NPC322021
0.6571 Remote Similarity NPC475828
0.6569 Remote Similarity NPC50548
0.6569 Remote Similarity NPC293624
0.6569 Remote Similarity NPC83019
0.6562 Remote Similarity NPC473748
0.6561 Remote Similarity NPC22472
0.6561 Remote Similarity NPC25495
0.6561 Remote Similarity NPC280680
0.6561 Remote Similarity NPC176300
0.6561 Remote Similarity NPC253634
0.6561 Remote Similarity NPC300943
0.6561 Remote Similarity NPC115798
0.6561 Remote Similarity NPC19687
0.6561 Remote Similarity NPC152166
0.6561 Remote Similarity NPC7846
0.6561 Remote Similarity NPC288669
0.6561 Remote Similarity NPC105242
0.6561 Remote Similarity NPC18607
0.6561 Remote Similarity NPC4481
0.6561 Remote Similarity NPC204854
0.6561 Remote Similarity NPC18772
0.6561 Remote Similarity NPC261004
0.6561 Remote Similarity NPC191459
0.6561 Remote Similarity NPC143828
0.6561 Remote Similarity NPC130894
0.6561 Remote Similarity NPC9609
0.6559 Remote Similarity NPC123886
0.6559 Remote Similarity NPC82325
0.6559 Remote Similarity NPC279989
0.6557 Remote Similarity NPC294972
0.6554 Remote Similarity NPC231572
0.6552 Remote Similarity NPC153453
0.655 Remote Similarity NPC123228
0.655 Remote Similarity NPC123722
0.655 Remote Similarity NPC151167
0.655 Remote Similarity NPC5018
0.655 Remote Similarity NPC276466
0.6543 Remote Similarity NPC55619
0.6543 Remote Similarity NPC200388
0.6543 Remote Similarity NPC265511
0.6543 Remote Similarity NPC100916
0.6541 Remote Similarity NPC295977
0.6541 Remote Similarity NPC58310
0.6538 Remote Similarity NPC287275
0.6534 Remote Similarity NPC106606
0.6532 Remote Similarity NPC66905
0.6529 Remote Similarity NPC3221
0.6524 Remote Similarity NPC86485
0.6524 Remote Similarity NPC57512
0.6522 Remote Similarity NPC195202
0.6522 Remote Similarity NPC261548
0.652 Remote Similarity NPC144314
0.652 Remote Similarity NPC204580
0.6519 Remote Similarity NPC160378
0.6514 Remote Similarity NPC327410
0.6509 Remote Similarity NPC242372
0.6509 Remote Similarity NPC4181
0.6509 Remote Similarity NPC257976
0.6509 Remote Similarity NPC164778
0.6508 Remote Similarity NPC287979
0.6508 Remote Similarity NPC29841
0.6508 Remote Similarity NPC112954
0.6508 Remote Similarity NPC78302
0.6508 Remote Similarity NPC227192
0.6508 Remote Similarity NPC189179
0.6508 Remote Similarity NPC110070
0.6508 Remote Similarity NPC235215
0.6508 Remote Similarity NPC75215
0.6508 Remote Similarity NPC305663
0.6508 Remote Similarity NPC163524
0.6508 Remote Similarity NPC224137
0.6508 Remote Similarity NPC472438
0.6508 Remote Similarity NPC101830
0.6508 Remote Similarity NPC93376
0.6508 Remote Similarity NPC176665
0.6508 Remote Similarity NPC7973
0.6508 Remote Similarity NPC203891
0.6505 Remote Similarity NPC200740
0.6505 Remote Similarity NPC125062
0.6505 Remote Similarity NPC306011
0.6505 Remote Similarity NPC50403
0.6505 Remote Similarity NPC28274
0.6505 Remote Similarity NPC472838
0.6505 Remote Similarity NPC252933
0.6505 Remote Similarity NPC54394
0.6505 Remote Similarity NPC133953
0.65 Remote Similarity NPC472410
0.6491 Remote Similarity NPC179777
0.6485 Remote Similarity NPC196231
0.648 Remote Similarity NPC288452
0.648 Remote Similarity NPC191280
0.648 Remote Similarity NPC289690
0.6477 Remote Similarity NPC196708
0.6474 Remote Similarity NPC200555
0.6474 Remote Similarity NPC196026
0.6474 Remote Similarity NPC193842
0.6474 Remote Similarity NPC304622
0.6471 Remote Similarity NPC312404
0.6471 Remote Similarity NPC301123
0.6471 Remote Similarity NPC273686
0.6471 Remote Similarity NPC55205
0.6471 Remote Similarity NPC134677
0.6471 Remote Similarity NPC149962
0.6467 Remote Similarity NPC33265
0.6467 Remote Similarity NPC62536
0.6467 Remote Similarity NPC12200
0.6467 Remote Similarity NPC1580
0.6464 Remote Similarity NPC169214
0.6464 Remote Similarity NPC141817
0.6464 Remote Similarity NPC176030
0.6464 Remote Similarity NPC192597
0.6464 Remote Similarity NPC229218
0.6459 Remote Similarity NPC477666
0.6458 Remote Similarity NPC78332
0.6458 Remote Similarity NPC196091
0.6455 Remote Similarity NPC98661
0.6455 Remote Similarity NPC247017
0.6455 Remote Similarity NPC245546
0.6455 Remote Similarity NPC292107
0.6455 Remote Similarity NPC474520
0.6455 Remote Similarity NPC268161
0.6455 Remote Similarity NPC471985
0.6455 Remote Similarity NPC49824
0.6455 Remote Similarity NPC266960
0.6455 Remote Similarity NPC43243
0.6453 Remote Similarity NPC16651
0.6453 Remote Similarity NPC32163
0.6452 Remote Similarity NPC58661
0.6452 Remote Similarity NPC476580
0.6452 Remote Similarity NPC286342
0.6452 Remote Similarity NPC149127
0.6452 Remote Similarity NPC300329
0.6452 Remote Similarity NPC188871
0.645 Remote Similarity NPC114298
0.6448 Remote Similarity NPC324081
0.6444 Remote Similarity NPC28398
0.6442 Remote Similarity NPC140577
0.6442 Remote Similarity NPC232533
0.6442 Remote Similarity NPC43069
0.6441 Remote Similarity NPC204592
0.6441 Remote Similarity NPC139519

  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 NPC471847 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
0.6927 Remote Similarity NPD7132 Clinical (unspecified phase)
0.691 Remote Similarity NPD3688 Clinical (unspecified phase)
0.691 Remote Similarity NPD3146 Approved
0.6667 Remote Similarity NPD5676 Approved
0.6633 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6585 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6584 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6576 Remote Similarity NPD3866 Clinical (unspecified phase)
0.6557 Remote Similarity NPD7131 Phase 3
0.6552 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6515 Remote Similarity NPD6853 Approved
0.6515 Remote Similarity NPD6851 Approved
0.6505 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6505 Remote Similarity NPD7110 Phase 1
0.6486 Remote Similarity NPD824 Approved
0.648 Remote Similarity NPD6297 Approved
0.6467 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6459 Remote Similarity NPD7891 Discontinued
0.645 Remote Similarity NPD6793 Clinical (unspecified phase)
0.645 Remote Similarity NPD4084 Clinical (unspecified phase)
0.6442 Remote Similarity NPD3533 Approved
0.6442 Remote Similarity NPD2972 Approved
0.6442 Remote Similarity NPD2491 Approved
0.6402 Remote Similarity NPD3817 Phase 2
0.6392 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6392 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6392 Remote Similarity NPD6166 Phase 2
0.6368 Remote Similarity NPD3882 Suspended
0.6368 Remote Similarity NPD7585 Approved
0.6364 Remote Similarity NPD7039 Approved
0.6364 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3057 Approved
0.6364 Remote Similarity NPD6875 Approved
0.6364 Remote Similarity NPD7038 Approved
0.6364 Remote Similarity NPD3448 Approved
0.6364 Remote Similarity NPD6876 Approved
0.6355 Remote Similarity NPD2490 Approved
0.6355 Remote Similarity NPD2488 Approved
0.6349 Remote Similarity NPD2801 Approved
0.6346 Remote Similarity NPD5457 Discontinued
0.6339 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6332 Remote Similarity NPD7808 Phase 3
0.633 Remote Similarity NPD6385 Approved
0.633 Remote Similarity NPD6386 Approved
0.6327 Remote Similarity NPD2163 Approved
0.6324 Remote Similarity NPD1512 Approved
0.6321 Remote Similarity NPD7583 Approved
0.6319 Remote Similarity NPD5481 Discontinued
0.6313 Remote Similarity NPD6797 Phase 2
0.6307 Remote Similarity NPD5745 Approved
0.6305 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6298 Remote Similarity NPD7811 Phase 3
0.6298 Remote Similarity NPD7810 Phase 3
0.6281 Remote Similarity NPD7251 Discontinued
0.6271 Remote Similarity NPD3142 Approved
0.6271 Remote Similarity NPD3140 Approved
0.6269 Remote Similarity NPD3251 Approved
0.6262 Remote Similarity NPD7256 Discontinued
0.6256 Remote Similarity NPD7291 Discontinued
0.6245 Remote Similarity NPD7048 Phase 3
0.6244 Remote Similarity NPD7584 Approved
0.6238 Remote Similarity NPD4482 Phase 3
0.6238 Remote Similarity NPD2493 Approved
0.6238 Remote Similarity NPD2494 Approved
0.6237 Remote Similarity NPD8127 Discontinued
0.623 Remote Similarity NPD4110 Phase 3
0.623 Remote Similarity NPD5977 Approved
0.623 Remote Similarity NPD5978 Approved
0.623 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6226 Remote Similarity NPD4582 Approved
0.6226 Remote Similarity NPD4583 Approved
0.6224 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6223 Remote Similarity NPD3455 Phase 2
0.6223 Remote Similarity NPD3769 Discontinued
0.6221 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6219 Remote Similarity NPD7281 Phase 3
0.6219 Remote Similarity NPD7280 Phase 3
0.6218 Remote Similarity NPD6862 Phase 2
0.6216 Remote Similarity NPD1511 Approved
0.6216 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6212 Remote Similarity NPD7054 Approved
0.6211 Remote Similarity NPD1934 Approved
0.6211 Remote Similarity NPD7577 Discontinued
0.6209 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6205 Remote Similarity NPD7608 Discontinued
0.6203 Remote Similarity NPD2122 Discontinued
0.6202 Remote Similarity NPD2973 Approved
0.6202 Remote Similarity NPD2975 Approved
0.6202 Remote Similarity NPD2974 Approved
0.6193 Remote Similarity NPD5746 Approved
0.619 Remote Similarity NPD4580 Approved
0.619 Remote Similarity NPD7255 Clinical (unspecified phase)
0.619 Remote Similarity NPD4107 Approved
0.6188 Remote Similarity NPD1725 Approved
0.6188 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6183 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6181 Remote Similarity NPD7472 Approved
0.6179 Remote Similarity NPD4004 Approved
0.6179 Remote Similarity NPD4002 Approved
0.6176 Remote Similarity NPD4157 Discontinued
0.6175 Remote Similarity NPD4236 Phase 3
0.6175 Remote Similarity NPD4237 Approved
0.6175 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6173 Remote Similarity NPD5242 Approved
0.6171 Remote Similarity NPD9494 Approved
0.6171 Remote Similarity NPD7907 Approved
0.6169 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6169 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6164 Remote Similarity NPD8149 Discontinued
0.6162 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6161 Remote Similarity NPD3450 Approved
0.6161 Remote Similarity NPD7476 Discontinued
0.6161 Remote Similarity NPD3452 Approved
0.6158 Remote Similarity NPD6873 Phase 2
0.615 Remote Similarity NPD4040 Phase 1
0.6146 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6146 Remote Similarity NPD5353 Approved
0.6139 Remote Similarity NPD2971 Approved
0.6139 Remote Similarity NPD2968 Approved
0.6135 Remote Similarity NPD4466 Phase 1
0.6135 Remote Similarity NPD6181 Discontinued
0.6129 Remote Similarity NPD5297 Approved
0.6127 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6126 Remote Similarity NPD6844 Discontinued
0.6121 Remote Similarity NPD7607 Clinical (unspecified phase)
0.6119 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6117 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6720 Clinical (unspecified phase)
0.6111 Remote Similarity NPD2653 Approved
0.6108 Remote Similarity NPD6618 Phase 2
0.6106 Remote Similarity NPD3473 Clinical (unspecified phase)
0.61 Remote Similarity NPD7074 Phase 3
0.6096 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6096 Remote Similarity NPD3536 Discontinued
0.6094 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6094 Remote Similarity NPD5773 Approved
0.6094 Remote Similarity NPD5772 Approved
0.6093 Remote Similarity NPD6296 Discontinued
0.6093 Remote Similarity NPD7263 Phase 2
0.6087 Remote Similarity NPD4162 Approved
0.6087 Remote Similarity NPD3060 Approved
0.6085 Remote Similarity NPD3687 Approved
0.6085 Remote Similarity NPD4124 Clinical (unspecified phase)
0.6085 Remote Similarity NPD3686 Approved
0.6083 Remote Similarity NPD5914 Approved
0.6081 Remote Similarity NPD4111 Phase 1
0.6081 Remote Similarity NPD4665 Approved
0.608 Remote Similarity NPD7177 Discontinued
0.6073 Remote Similarity NPD6677 Suspended
0.6073 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6071 Remote Similarity NPD2821 Approved
0.607 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6067 Remote Similarity NPD5718 Phase 2
0.6061 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6061 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6054 Remote Similarity NPD6331 Phase 2
0.6053 Remote Similarity NPD2649 Approved
0.6053 Remote Similarity NPD2651 Approved
0.6045 Remote Similarity NPD2614 Approved
0.6045 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6044 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6044 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6043 Remote Similarity NPD1774 Approved
0.6042 Remote Similarity NPD5722 Discontinued
0.6032 Remote Similarity NPD3639 Approved
0.6032 Remote Similarity NPD3640 Phase 3
0.6032 Remote Similarity NPD3641 Approved
0.6031 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6031 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6023 Remote Similarity NPD6584 Phase 3
0.6022 Remote Similarity NPD5241 Discontinued
0.6022 Remote Similarity NPD2219 Phase 1
0.6021 Remote Similarity NPD7028 Phase 2
0.602 Remote Similarity NPD2325 Approved
0.6019 Remote Similarity NPD5071 Phase 2
0.6011 Remote Similarity NPD2438 Suspended
0.6011 Remote Similarity NPD4123 Phase 3
0.6011 Remote Similarity NPD2239 Approved
0.6011 Remote Similarity NPD2240 Approved
0.6011 Remote Similarity NPD7095 Approved
0.601 Remote Similarity NPD7972 Discontinued
0.601 Remote Similarity NPD2388 Discontinued
0.601 Remote Similarity NPD6818 Clinical (unspecified phase)
0.601 Remote Similarity NPD3936 Clinical (unspecified phase)
0.6 Remote Similarity NPD1307 Phase 2
0.6 Remote Similarity NPD1309 Phase 2
0.6 Remote Similarity NPD8031 Discontinued
0.6 Remote Similarity NPD826 Approved
0.6 Remote Similarity NPD4210 Discontinued
0.6 Remote Similarity NPD3818 Discontinued
0.6 Remote Similarity NPD5536 Phase 2
0.6 Remote Similarity NPD7075 Discontinued
0.6 Remote Similarity NPD825 Approved
0.599 Remote Similarity NPD7484 Phase 3
0.599 Remote Similarity NPD7993 Clinical (unspecified phase)
0.599 Remote Similarity NPD7485 Phase 3
0.5988 Remote Similarity NPD2423 Clinical (unspecified phase)
0.5979 Remote Similarity NPD7318 Phase 3
0.5979 Remote Similarity NPD5967 Approved
0.5978 Remote Similarity NPD3268 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
A: chemistry similarity;
B: biological targets similarity;
C: networks similarity;
D: cell-based bioactivity similarity;
E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data