Structure

Physi-Chem Properties

Molecular Weight:  680.22
Volume:  655.83
LogP:  4.003
LogD:  1.336
LogS:  -0.927
# Rotatable Bonds:  10
TPSA:  212.42
# H-Bond Aceptor:  15
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.062
Synthetic Accessibility Score:  5.073
Fsp3:  0.353
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.148
MDCK Permeability:  1.646518285269849e-05
Pgp-inhibitor:  0.961
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.967
20% Bioavailability (F20%):  0.975
30% Bioavailability (F30%):  0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.031
Plasma Protein Binding (PPB):  99.81929016113281%
Volume Distribution (VD):  0.924
Pgp-substrate:  4.227432727813721%

ADMET: Metabolism

CYP1A2-inhibitor:  0.063
CYP1A2-substrate:  0.043
CYP2C19-inhibitor:  0.1
CYP2C19-substrate:  0.062
CYP2C9-inhibitor:  0.898
CYP2C9-substrate:  0.955
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.089
CYP3A4-inhibitor:  0.283
CYP3A4-substrate:  0.943

ADMET: Excretion

Clearance (CL):  4.784
Half-life (T1/2):  0.898

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.635
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.964
Maximum Recommended Daily Dose:  0.672
Skin Sensitization:  0.05
Carcinogencity:  0.689
Eye Corrosion:  0.003
Eye Irritation:  0.037
Respiratory Toxicity:  0.036

Download Data

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

  Natural Product: NPC119291

Natural Product ID:  NPC119291
Common Name*:   Sarcodonin Alpha
IUPAC Name:   [3-[(5S,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]-2-acetyloxy-4,5-dihydroxy-6-(4-hydroxyphenyl)phenyl] acetate
Synonyms:  
Standard InCHIKey:  ZRUOGCKQVBXKOD-JDRFZWGMSA-N
Standard InCHI:  InChI=1S/C34H36N2O13/c1-7-16(3)27-32(42)36(45)34(17(4)8-2,33(43)35(27)44)48-24-15-21(11-14-23(24)49-36)26-29(41)28(40)25(20-9-12-22(39)13-10-20)30(46-18(5)37)31(26)47-19(6)38/h9-17,39-42,44H,7-8H2,1-6H3/t16-,17+,34+,36-/m0/s1
SMILES:  CC[C@H]([C@@]12Oc3cc(ccc3ON2(=O)C(=C(N(C1=O)O)[C@H](CC)C)O)c1c(O)c(O)c(c(c1OC(=O)C)OC(=O)C)c1ccc(cc1)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3238012
PubChem CID:   90671617
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000041] Biphenyls 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 = 18000.0 nM PMID[539165]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 167.0 U PMID[539165]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 29000.0 nM PMID[539165]
NPT625 Tissue Liver Mus musculus IC50 = 73000.0 nM PMID[539165]
NPT2 Others Unspecified IC50 = 1230.0 nM PMID[539165]

☑ 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 NPC119291 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 NPC471849
1.0 High Similarity NPC161144
1.0 High Similarity NPC471848
0.8245 Intermediate Similarity NPC18633
0.8245 Intermediate Similarity NPC471847
0.7166 Intermediate Similarity NPC113790
0.7135 Intermediate Similarity NPC36077
0.712 Intermediate Similarity NPC292385
0.712 Intermediate Similarity NPC125709
0.7098 Intermediate Similarity NPC36354
0.7087 Intermediate Similarity NPC471563
0.707 Intermediate Similarity NPC92235
0.7059 Intermediate Similarity NPC170239
0.7059 Intermediate Similarity NPC275125
0.7059 Intermediate Similarity NPC97937
0.7005 Intermediate Similarity NPC475896
0.699 Remote Similarity NPC140346
0.699 Remote Similarity NPC174311
0.6979 Remote Similarity NPC7178
0.6979 Remote Similarity NPC62903
0.6976 Remote Similarity NPC29531
0.6968 Remote Similarity NPC231149
0.6952 Remote Similarity NPC292256
0.6952 Remote Similarity NPC125617
0.6943 Remote Similarity NPC155015
0.6943 Remote Similarity NPC142479
0.694 Remote Similarity NPC476171
0.693 Remote Similarity NPC185031
0.6923 Remote Similarity NPC252095
0.6904 Remote Similarity NPC55121
0.6904 Remote Similarity NPC476200
0.6904 Remote Similarity NPC192258
0.6898 Remote Similarity NPC185127
0.6856 Remote Similarity NPC316292
0.6848 Remote Similarity NPC105493
0.6845 Remote Similarity NPC7439
0.6845 Remote Similarity NPC256555
0.6845 Remote Similarity NPC34245
0.6845 Remote Similarity NPC91492
0.6845 Remote Similarity NPC110067
0.6842 Remote Similarity NPC139839
0.6842 Remote Similarity NPC48366
0.6839 Remote Similarity NPC476154
0.6813 Remote Similarity NPC474810
0.6806 Remote Similarity NPC176903
0.6806 Remote Similarity NPC30688
0.68 Remote Similarity NPC471823
0.6788 Remote Similarity NPC163598
0.6788 Remote Similarity NPC120774
0.6788 Remote Similarity NPC264875
0.6786 Remote Similarity NPC44040
0.6771 Remote Similarity NPC294522
0.6771 Remote Similarity NPC205727
0.6771 Remote Similarity NPC120426
0.6771 Remote Similarity NPC21184
0.6768 Remote Similarity NPC124747
0.6768 Remote Similarity NPC109061
0.6768 Remote Similarity NPC155754
0.6758 Remote Similarity NPC474635
0.6755 Remote Similarity NPC236419
0.6755 Remote Similarity NPC230157
0.6754 Remote Similarity NPC315914
0.6748 Remote Similarity NPC475566
0.6742 Remote Similarity NPC473746
0.6733 Remote Similarity NPC476637
0.6733 Remote Similarity NPC280493
0.6733 Remote Similarity NPC476279
0.6719 Remote Similarity NPC476969
0.6718 Remote Similarity NPC268484
0.6718 Remote Similarity NPC80918
0.6718 Remote Similarity NPC188578
0.6717 Remote Similarity NPC130955
0.6717 Remote Similarity NPC301089
0.6703 Remote Similarity NPC147317
0.6703 Remote Similarity NPC142530
0.6702 Remote Similarity NPC472332
0.6702 Remote Similarity NPC469564
0.6702 Remote Similarity NPC472335
0.67 Remote Similarity NPC265214
0.6699 Remote Similarity NPC226725
0.6697 Remote Similarity NPC257728
0.6696 Remote Similarity NPC211215
0.6684 Remote Similarity NPC476642
0.6683 Remote Similarity NPC99591
0.6682 Remote Similarity NPC475180
0.6667 Remote Similarity NPC94220
0.6667 Remote Similarity NPC24339
0.6667 Remote Similarity NPC187398
0.6667 Remote Similarity NPC7543
0.6667 Remote Similarity NPC148835
0.6667 Remote Similarity NPC85057
0.6667 Remote Similarity NPC20511
0.6667 Remote Similarity NPC142614
0.6667 Remote Similarity NPC473748
0.6667 Remote Similarity NPC153365
0.6667 Remote Similarity NPC139548
0.6667 Remote Similarity NPC52086
0.6667 Remote Similarity NPC76336
0.6667 Remote Similarity NPC223720
0.6667 Remote Similarity NPC130920
0.6667 Remote Similarity NPC476348
0.6667 Remote Similarity NPC475669
0.6667 Remote Similarity NPC83019
0.6667 Remote Similarity NPC38874
0.6667 Remote Similarity NPC166456
0.6667 Remote Similarity NPC95162
0.6667 Remote Similarity NPC98083
0.6651 Remote Similarity NPC154527
0.6651 Remote Similarity NPC257266
0.665 Remote Similarity NPC284810
0.665 Remote Similarity NPC67424
0.665 Remote Similarity NPC165483
0.6636 Remote Similarity NPC477666
0.6635 Remote Similarity NPC41845
0.6635 Remote Similarity NPC6709
0.6634 Remote Similarity NPC9309
0.6633 Remote Similarity NPC8712
0.6632 Remote Similarity NPC10010
0.6631 Remote Similarity NPC25966
0.6631 Remote Similarity NPC127218
0.6631 Remote Similarity NPC13067
0.6631 Remote Similarity NPC245207
0.6631 Remote Similarity NPC319647
0.663 Remote Similarity NPC277021
0.662 Remote Similarity NPC204580
0.662 Remote Similarity NPC281629
0.6618 Remote Similarity NPC109827
0.6618 Remote Similarity NPC297807
0.6618 Remote Similarity NPC72696
0.6618 Remote Similarity NPC101107
0.6618 Remote Similarity NPC124470
0.6618 Remote Similarity NPC98546
0.6616 Remote Similarity NPC125495
0.6615 Remote Similarity NPC15577
0.6615 Remote Similarity NPC160196
0.6615 Remote Similarity NPC476347
0.6613 Remote Similarity NPC126682
0.6613 Remote Similarity NPC82271
0.6605 Remote Similarity NPC469689
0.6605 Remote Similarity NPC471031
0.6603 Remote Similarity NPC234069
0.6601 Remote Similarity NPC10871
0.66 Remote Similarity NPC177100
0.66 Remote Similarity NPC139540
0.6595 Remote Similarity NPC474600
0.6589 Remote Similarity NPC50548
0.6588 Remote Similarity NPC174486
0.6585 Remote Similarity NPC32064
0.6584 Remote Similarity NPC156432
0.6583 Remote Similarity NPC130894
0.6583 Remote Similarity NPC143828
0.6583 Remote Similarity NPC9609
0.6583 Remote Similarity NPC18607
0.6583 Remote Similarity NPC4481
0.6583 Remote Similarity NPC7846
0.6583 Remote Similarity NPC115798
0.6583 Remote Similarity NPC300943
0.6583 Remote Similarity NPC176300
0.6583 Remote Similarity NPC261004
0.6583 Remote Similarity NPC18772
0.6583 Remote Similarity NPC152166
0.6583 Remote Similarity NPC288669
0.6583 Remote Similarity NPC19687
0.6583 Remote Similarity NPC253634
0.6583 Remote Similarity NPC22472
0.6583 Remote Similarity NPC191459
0.6583 Remote Similarity NPC204854
0.6583 Remote Similarity NPC105242
0.6583 Remote Similarity NPC25495
0.6582 Remote Similarity NPC150442
0.6582 Remote Similarity NPC149735
0.658 Remote Similarity NPC281549
0.658 Remote Similarity NPC477879
0.6579 Remote Similarity NPC477616
0.6578 Remote Similarity NPC474886
0.6578 Remote Similarity NPC276490
0.6571 Remote Similarity NPC470451
0.6571 Remote Similarity NPC174122
0.6571 Remote Similarity NPC64140
0.6571 Remote Similarity NPC470455
0.657 Remote Similarity NPC216307
0.6569 Remote Similarity NPC475805
0.6567 Remote Similarity NPC471745
0.6567 Remote Similarity NPC8300
0.6566 Remote Similarity NPC55619
0.6566 Remote Similarity NPC200388
0.6566 Remote Similarity NPC100916
0.6564 Remote Similarity NPC213197
0.6562 Remote Similarity NPC287275
0.6562 Remote Similarity NPC205361
0.6561 Remote Similarity NPC471389
0.6555 Remote Similarity NPC47883
0.6553 Remote Similarity NPC470942
0.6553 Remote Similarity NPC329816
0.6552 Remote Similarity NPC470462
0.655 Remote Similarity NPC155101
0.6548 Remote Similarity NPC77430
0.6543 Remote Similarity NPC19869
0.6543 Remote Similarity NPC43500
0.6543 Remote Similarity NPC164148

  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 NPC119291 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
0.6765 Remote Similarity NPD7549 Discontinued
0.6697 Remote Similarity NPD7585 Approved
0.6684 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6651 Remote Similarity NPD7583 Approved
0.6633 Remote Similarity NPD5677 Discontinued
0.662 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6618 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6495 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6462 Remote Similarity NPD1653 Approved
0.6442 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6436 Remote Similarity NPD8127 Discontinued
0.6432 Remote Similarity NPD3817 Phase 2
0.6429 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6408 Remote Similarity NPD5844 Phase 1
0.6406 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6392 Remote Similarity NPD7447 Phase 1
0.6392 Remote Similarity NPD3146 Approved
0.6392 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6386 Remote Similarity NPD4666 Phase 3
0.6382 Remote Similarity NPD2801 Approved
0.6381 Remote Similarity NPD8054 Approved
0.6381 Remote Similarity NPD8053 Approved
0.6376 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6373 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6368 Remote Similarity NPD7906 Approved
0.6364 Remote Similarity NPD7808 Phase 3
0.6359 Remote Similarity NPD7228 Approved
0.6354 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6352 Remote Similarity NPD8153 Approved
0.6352 Remote Similarity NPD8152 Approved
0.6348 Remote Similarity NPD7907 Approved
0.6347 Remote Similarity NPD2494 Approved
0.6347 Remote Similarity NPD2493 Approved
0.6341 Remote Similarity NPD6166 Phase 2
0.6341 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6341 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6337 Remote Similarity NPD6234 Discontinued
0.6337 Remote Similarity NPD5709 Phase 3
0.6335 Remote Similarity NPD4582 Approved
0.6335 Remote Similarity NPD4583 Approved
0.6335 Remote Similarity NPD7891 Discontinued
0.6333 Remote Similarity NPD7311 Approved
0.6333 Remote Similarity NPD7313 Approved
0.6333 Remote Similarity NPD7312 Approved
0.6333 Remote Similarity NPD7310 Approved
0.6318 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7251 Discontinued
0.6303 Remote Similarity NPD7309 Approved
0.63 Remote Similarity NPD1465 Phase 2
0.629 Remote Similarity NPD4002 Approved
0.629 Remote Similarity NPD4004 Approved
0.6287 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6286 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6278 Remote Similarity NPD7584 Approved
0.6278 Remote Similarity NPD7263 Phase 2
0.6276 Remote Similarity NPD7048 Phase 3
0.6273 Remote Similarity NPD3452 Approved
0.6273 Remote Similarity NPD3450 Approved
0.627 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6269 Remote Similarity NPD5402 Approved
0.6268 Remote Similarity NPD6797 Phase 2
0.6268 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6262 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6262 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6256 Remote Similarity NPD7213 Phase 3
0.6256 Remote Similarity NPD7212 Phase 2
0.625 Remote Similarity NPD7054 Approved
0.6244 Remote Similarity NPD6793 Clinical (unspecified phase)
0.6239 Remote Similarity NPD5676 Approved
0.6238 Remote Similarity NPD7038 Approved
0.6238 Remote Similarity NPD7039 Approved
0.6237 Remote Similarity NPD2219 Phase 1
0.6232 Remote Similarity NPD7473 Discontinued
0.6226 Remote Similarity NPD6851 Approved
0.6226 Remote Similarity NPD6853 Approved
0.6225 Remote Similarity NPD6746 Phase 2
0.6223 Remote Similarity NPD5619 Clinical (unspecified phase)
0.622 Remote Similarity NPD7074 Phase 3
0.622 Remote Similarity NPD7472 Approved
0.6216 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5242 Approved
0.6212 Remote Similarity NPD3687 Approved
0.6212 Remote Similarity NPD3686 Approved
0.6201 Remote Similarity NPD7047 Phase 3
0.6197 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6195 Remote Similarity NPD7199 Phase 2
0.6193 Remote Similarity NPD1512 Approved
0.619 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6178 Remote Similarity NPD7701 Phase 2
0.6169 Remote Similarity NPD37 Approved
0.6169 Remote Similarity NPD1934 Approved
0.6168 Remote Similarity NPD4663 Approved
0.6167 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6167 Remote Similarity NPD7783 Phase 2
0.6165 Remote Similarity NPD6232 Discontinued
0.6164 Remote Similarity NPD2974 Approved
0.6164 Remote Similarity NPD2973 Approved
0.6164 Remote Similarity NPD2975 Approved
0.6158 Remote Similarity NPD4967 Phase 2
0.6158 Remote Similarity NPD4966 Approved
0.6158 Remote Similarity NPD3882 Suspended
0.6158 Remote Similarity NPD4965 Approved
0.6157 Remote Similarity NPD2490 Approved
0.6157 Remote Similarity NPD2488 Approved
0.6154 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4580 Approved
0.6151 Remote Similarity NPD6723 Discontinued
0.6142 Remote Similarity NPD1754 Clinical (unspecified phase)
0.614 Remote Similarity NPD7827 Phase 1
0.6138 Remote Similarity NPD1613 Approved
0.6138 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6127 Remote Similarity NPD7075 Discontinued
0.6126 Remote Similarity NPD7476 Discontinued
0.6122 Remote Similarity NPD6667 Approved
0.6122 Remote Similarity NPD6666 Approved
0.6121 Remote Similarity NPD4111 Phase 1
0.6121 Remote Similarity NPD4665 Approved
0.6114 Remote Similarity NPD6297 Approved
0.6108 Remote Similarity NPD5353 Approved
0.6106 Remote Similarity NPD4481 Phase 3
0.6103 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6103 Remote Similarity NPD4578 Approved
0.6103 Remote Similarity NPD3750 Approved
0.6103 Remote Similarity NPD4577 Approved
0.6095 Remote Similarity NPD42 Phase 2
0.6095 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6095 Remote Similarity NPD6042 Phase 2
0.6091 Remote Similarity NPD1774 Approved
0.6091 Remote Similarity NPD1511 Approved
0.6091 Remote Similarity NPD5297 Approved
0.6087 Remote Similarity NPD7608 Discontinued
0.6087 Remote Similarity NPD4749 Approved
0.6073 Remote Similarity NPD7256 Discontinued
0.607 Remote Similarity NPD4675 Approved
0.607 Remote Similarity NPD4678 Approved
0.6068 Remote Similarity NPD3251 Approved
0.6068 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6064 Remote Similarity NPD7095 Approved
0.6064 Remote Similarity NPD3027 Phase 3
0.6062 Remote Similarity NPD6099 Approved
0.6062 Remote Similarity NPD6100 Approved
0.6061 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6061 Remote Similarity NPD3536 Discontinued
0.6059 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6054 Remote Similarity NPD4482 Phase 3
0.6053 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6053 Remote Similarity NPD4060 Phase 1
0.6053 Remote Similarity NPD7874 Approved
0.605 Remote Similarity NPD4210 Discontinued
0.6048 Remote Similarity NPD3818 Discontinued
0.6048 Remote Similarity NPD8099 Discontinued
0.6048 Remote Similarity NPD8251 Approved
0.6048 Remote Similarity NPD8252 Approved
0.6044 Remote Similarity NPD8320 Phase 1
0.6044 Remote Similarity NPD8319 Approved
0.6043 Remote Similarity NPD6997 Phase 2
0.604 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6037 Remote Similarity NPD7235 Clinical (unspecified phase)
0.603 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6029 Remote Similarity NPD2489 Approved
0.6029 Remote Similarity NPD27 Approved
0.6028 Remote Similarity NPD7280 Phase 3
0.6028 Remote Similarity NPD7281 Phase 3
0.6027 Remote Similarity NPD3533 Approved
0.6027 Remote Similarity NPD2972 Approved
0.6027 Remote Similarity NPD2491 Approved
0.6021 Remote Similarity NPD6355 Discontinued
0.602 Remote Similarity NPD4109 Clinical (unspecified phase)
0.602 Remote Similarity NPD4110 Phase 3
0.6019 Remote Similarity NPD8156 Discontinued
0.6019 Remote Similarity NPD8150 Discontinued
0.6009 Remote Similarity NPD7240 Approved
0.6 Remote Similarity NPD5403 Approved
0.6 Remote Similarity NPD2122 Discontinued
0.6 Remote Similarity NPD5745 Approved
0.6 Remote Similarity NPD8366 Approved
0.599 Remote Similarity NPD6599 Discontinued
0.5982 Remote Similarity NPD7879 Clinical (unspecified phase)
0.5981 Remote Similarity NPD2970 Approved
0.5981 Remote Similarity NPD4419 Clinical (unspecified phase)
0.5981 Remote Similarity NPD2969 Approved
0.598 Remote Similarity NPD6818 Clinical (unspecified phase)
0.598 Remote Similarity NPD5773 Approved
0.598 Remote Similarity NPD6668 Clinical (unspecified phase)
0.598 Remote Similarity NPD7096 Clinical (unspecified phase)
0.598 Remote Similarity NPD7972 Discontinued
0.598 Remote Similarity NPD5772 Approved
0.5979 Remote Similarity NPD6032 Approved
0.5978 Remote Similarity NPD422 Phase 1
0.5973 Remote Similarity NPD4040 Phase 1
0.5972 Remote Similarity NPD5940 Clinical (unspecified phase)
0.5972 Remote Similarity NPD6620 Discovery
0.5972 Remote Similarity NPD7177 Discontinued
0.5971 Remote Similarity NPD3453 Discontinued
0.5966 Remote Similarity NPD8491 Approved
0.5963 Remote Similarity NPD7861 Discontinued
0.5961 Remote Similarity NPD5089 Approved
0.5961 Remote Similarity NPD5090 Approved
0.596 Remote Similarity NPD7124 Phase 2
0.5959 Remote Similarity NPD6111 Discontinued

  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