Natural Product: NPC325297

Natural Product ID:  NPC325297
Common Name:   5,6-Dihydroxyindole-2-Carboxylic Acid
IUPAC Name:   5,6-dihydroxy-1H-indole-2-carboxylic acid
Synonyms:  
Molecular Formula:   C9H7NO4
Standard InCHIKey:  YFTGOBNOJKXZJC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)
Canonical SMILES:  Oc1cc2[nH]c(cc2cc1O)C(=O)O
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO20338 Mus musculus Species Muridae Eukaryota PMID[19425150]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT23 Individual Protein Integrase Human immunodeficiency virus 1 IC50 < 10000 nM 17367896
NPT1627 Individual Protein G-protein coupled receptor 35 Homo sapiens EC50 = 23600 nM 24900508
NPT1627 Individual Protein G-protein coupled receptor 35 Homo sapiens EC50 = 23200 nM 24900508

  Similar Natural Products 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 NPC325297 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
0.868 High Similarity NPC321428
0.8274 Intermediate Similarity NPC306376
0.8267 Intermediate Similarity NPC39679
0.8214 Intermediate Similarity NPC276517
0.8159 Intermediate Similarity NPC476098
0.8128 Intermediate Similarity NPC270918
0.8122 Intermediate Similarity NPC326634
0.8069 Intermediate Similarity NPC134848
0.8058 Intermediate Similarity NPC294375
0.8058 Intermediate Similarity NPC87413
0.8039 Intermediate Similarity NPC244741
0.801 Intermediate Similarity NPC144381
0.801 Intermediate Similarity NPC213308
0.8 Intermediate Similarity NPC86834
0.8 Intermediate Similarity NPC210828
0.799 Intermediate Similarity NPC3207
0.7943 Intermediate Similarity NPC118228
0.7921 Intermediate Similarity NPC315491
0.7921 Intermediate Similarity NPC45459
0.7885 Intermediate Similarity NPC23294
0.7864 Intermediate Similarity NPC283117
0.7864 Intermediate Similarity NPC88008
0.7864 Intermediate Similarity NPC4687
0.7861 Intermediate Similarity NPC141454
0.786 Intermediate Similarity NPC179287
0.7843 Intermediate Similarity NPC135887
0.7843 Intermediate Similarity NPC199277
0.784 Intermediate Similarity NPC174760
0.7837 Intermediate Similarity NPC303951
0.7822 Intermediate Similarity NPC472284
0.7816 Intermediate Similarity NPC300156
0.7814 Intermediate Similarity NPC51388
0.781 Intermediate Similarity NPC89508
0.7805 Intermediate Similarity NPC165599
0.7799 Intermediate Similarity NPC9894
0.7778 Intermediate Similarity NPC160898
0.7778 Intermediate Similarity NPC183777
0.7748 Intermediate Similarity NPC15801
0.7746 Intermediate Similarity NPC184408
0.77 Intermediate Similarity NPC293151
0.77 Intermediate Similarity NPC312645
0.7678 Intermediate Similarity NPC12344
0.7664 Intermediate Similarity NPC46561
0.7664 Intermediate Similarity NPC247803
0.7656 Intermediate Similarity NPC171787
0.7628 Intermediate Similarity NPC208084
0.7628 Intermediate Similarity NPC74360
0.7626 Intermediate Similarity NPC241025
0.7624 Intermediate Similarity NPC230403
0.7617 Intermediate Similarity NPC169402
0.7609 Intermediate Similarity NPC473800
0.7608 Intermediate Similarity NPC249583
0.7606 Intermediate Similarity NPC116238
0.7602 Intermediate Similarity NPC474701
0.7598 Intermediate Similarity NPC156704
0.7594 Intermediate Similarity NPC219087
0.7593 Intermediate Similarity NPC150239
0.7591 Intermediate Similarity NPC274640
0.7591 Intermediate Similarity NPC194740
0.7566 Intermediate Similarity NPC322644
0.756 Intermediate Similarity NPC472286
0.756 Intermediate Similarity NPC472287
0.756 Intermediate Similarity NPC45190
0.7559 Intermediate Similarity NPC39500
0.7551 Intermediate Similarity NPC72980
0.7526 Intermediate Similarity NPC474409
0.7512 Intermediate Similarity NPC221873
0.7512 Intermediate Similarity NPC153042
0.7512 Intermediate Similarity NPC276657
0.7512 Intermediate Similarity NPC316981
0.7511 Intermediate Similarity NPC6786
0.7511 Intermediate Similarity NPC178858
0.75 Intermediate Similarity NPC309845
0.75 Intermediate Similarity NPC264285
0.7488 Intermediate Similarity NPC330009
0.7488 Intermediate Similarity NPC469928
0.7487 Intermediate Similarity NPC303225
0.7478 Intermediate Similarity NPC82472
0.7475 Intermediate Similarity NPC83111
0.7463 Intermediate Similarity NPC46580
0.7462 Intermediate Similarity NPC88363
0.7458 Intermediate Similarity NPC89549
0.7443 Intermediate Similarity NPC144452
0.744 Intermediate Similarity NPC280714
0.7437 Intermediate Similarity NPC212535
0.743 Intermediate Similarity NPC308137
0.743 Intermediate Similarity NPC310211
0.7412 Intermediate Similarity NPC475844
0.7411 Intermediate Similarity NPC96890
0.7411 Intermediate Similarity NPC184964
0.7383 Intermediate Similarity NPC82370
0.7382 Intermediate Similarity NPC181081
0.7373 Intermediate Similarity NPC472285
0.7366 Intermediate Similarity NPC260434
0.7364 Intermediate Similarity NPC16352
0.7363 Intermediate Similarity NPC94943
0.7346 Intermediate Similarity NPC132539
0.7343 Intermediate Similarity NPC90229
0.7339 Intermediate Similarity NPC165964
0.7336 Intermediate Similarity NPC49672
0.7333 Intermediate Similarity NPC132329
0.7327 Intermediate Similarity NPC160381
0.7318 Intermediate Similarity NPC280799
0.7313 Intermediate Similarity NPC190007
0.7302 Intermediate Similarity NPC187501
0.7302 Intermediate Similarity NPC146418
0.7293 Intermediate Similarity NPC41501
0.7291 Intermediate Similarity NPC278434
0.7277 Intermediate Similarity NPC314002
0.7269 Intermediate Similarity NPC74619
0.7264 Intermediate Similarity NPC220765
0.726 Intermediate Similarity NPC303658
0.7257 Intermediate Similarity NPC207686
0.7248 Intermediate Similarity NPC322064
0.7248 Intermediate Similarity NPC74969
0.724 Intermediate Similarity NPC60621
0.7237 Intermediate Similarity NPC272549
0.7233 Intermediate Similarity NPC99666
0.7228 Intermediate Similarity NPC204717
0.7222 Intermediate Similarity NPC246518
0.7215 Intermediate Similarity NPC246658
0.7212 Intermediate Similarity NPC474688
0.7207 Intermediate Similarity NPC220851
0.7204 Intermediate Similarity NPC471944
0.7196 Intermediate Similarity NPC193777
0.7195 Intermediate Similarity NPC225279
0.7195 Intermediate Similarity NPC54066
0.7193 Intermediate Similarity NPC182222
0.7193 Intermediate Similarity NPC208898
0.7175 Intermediate Similarity NPC211416
0.7174 Intermediate Similarity NPC470784
0.7171 Intermediate Similarity NPC246700
0.7171 Intermediate Similarity NPC128751
0.7169 Intermediate Similarity NPC148183
0.7169 Intermediate Similarity NPC152768
0.7163 Intermediate Similarity NPC131017
0.7162 Intermediate Similarity NPC198503
0.7157 Intermediate Similarity NPC194040
0.7157 Intermediate Similarity NPC171171
0.7156 Intermediate Similarity NPC266931
0.715 Intermediate Similarity NPC15573
0.715 Intermediate Similarity NPC183662
0.715 Intermediate Similarity NPC217372
0.7136 Intermediate Similarity NPC469497
0.7136 Intermediate Similarity NPC106833
0.7136 Intermediate Similarity NPC27041
0.713 Intermediate Similarity NPC184680
0.7116 Intermediate Similarity NPC53344
0.7114 Intermediate Similarity NPC219336
0.7111 Intermediate Similarity NPC24370
0.7111 Intermediate Similarity NPC319232
0.7111 Intermediate Similarity NPC214142
0.7104 Intermediate Similarity NPC174576
0.71 Intermediate Similarity NPC470785
0.7098 Intermediate Similarity NPC229893
0.7098 Intermediate Similarity NPC122436
0.7095 Intermediate Similarity NPC74153
0.7095 Intermediate Similarity NPC70956
0.7095 Intermediate Similarity NPC243834
0.7089 Intermediate Similarity NPC473188
0.7089 Intermediate Similarity NPC57398
0.7087 Intermediate Similarity NPC473187
0.7087 Intermediate Similarity NPC57453
0.7085 Intermediate Similarity NPC121069
0.708 Intermediate Similarity NPC124920
0.708 Intermediate Similarity NPC261251
0.708 Intermediate Similarity NPC118559
0.708 Intermediate Similarity NPC34580
0.708 Intermediate Similarity NPC304307
0.7074 Intermediate Similarity NPC284888
0.7067 Intermediate Similarity NPC21638
0.7065 Intermediate Similarity NPC111275
0.7051 Intermediate Similarity NPC160100
0.7048 Intermediate Similarity NPC100547
0.7043 Intermediate Similarity NPC97902
0.7038 Intermediate Similarity NPC207620
0.7034 Intermediate Similarity NPC218388
0.7033 Intermediate Similarity NPC473821
0.7032 Intermediate Similarity NPC118940
0.7032 Intermediate Similarity NPC48353
0.703 Intermediate Similarity NPC283219
0.7027 Intermediate Similarity NPC96321
0.7027 Intermediate Similarity NPC473041
0.7024 Intermediate Similarity NPC295158
0.7018 Intermediate Similarity NPC322135
0.7018 Intermediate Similarity NPC223409
0.7018 Intermediate Similarity NPC95240
0.7013 Intermediate Similarity NPC477549
0.7011 Intermediate Similarity NPC169716
0.7009 Intermediate Similarity NPC171393
0.7009 Intermediate Similarity NPC295452
0.7005 Intermediate Similarity NPC18348
0.7004 Intermediate Similarity NPC478078
0.7 Intermediate Similarity NPC146724
0.7 Intermediate Similarity NPC303374
0.7 Intermediate Similarity NPC323198
0.7 Intermediate Similarity NPC323752
0.7 Intermediate Similarity NPC172222
0.6996 Remote Similarity NPC288987
0.6995 Remote Similarity NPC249040

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC325297 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
0.7921 Intermediate Similarity NPD484 Approved
0.7419 Intermediate Similarity NPD5632 Approved
0.7393 Intermediate Similarity NPD2715 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD2844 Phase 3
0.7264 Intermediate Similarity NPD2721 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5416 Discontinued
0.7217 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD3178 Discontinued
0.7156 Intermediate Similarity NPD3243 Approved
0.7149 Intermediate Similarity NPD3258 Approved
0.7103 Intermediate Similarity NPD5901 Discontinued
0.7083 Intermediate Similarity NPD5658 Approved
0.7083 Intermediate Similarity NPD2916 Discontinued
0.708 Intermediate Similarity NPD3259 Approved
0.7046 Intermediate Similarity NPD5482 Discontinued
0.7045 Intermediate Similarity NPD3257 Approved
0.7014 Intermediate Similarity NPD5003 Discontinued
0.7005 Intermediate Similarity NPD6376 Discontinued
0.7004 Intermediate Similarity NPD4845 Discontinued
0.7004 Intermediate Similarity NPD4328 Approved
0.6987 Remote Similarity NPD1505 Phase 2
0.6957 Remote Similarity NPD4885 Approved
0.6957 Remote Similarity NPD3746 Discontinued
0.6955 Remote Similarity NPD5866 Approved
0.6952 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6951 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6948 Remote Similarity NPD1768 Approved
0.6944 Remote Similarity NPD6138 Clinical (unspecified phase)
0.6942 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6937 Remote Similarity NPD5612 Discontinued
0.6926 Remote Similarity NPD4373 Phase 2
0.6926 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6913 Remote Similarity NPD6962 Phase 2
0.6911 Remote Similarity NPD7803 Approved
0.6891 Remote Similarity NPD3328 Phase 2
0.689 Remote Similarity NPD2564 Approved
0.689 Remote Similarity NPD2565 Phase 2
0.6889 Remote Similarity NPD6242 Discontinued
0.6886 Remote Similarity NPD7603 Discontinued
0.6881 Remote Similarity NPD482 Approved
0.6875 Remote Similarity NPD4948 Discontinued
0.6869 Remote Similarity NPD1631 Approved
0.6864 Remote Similarity NPD648 Clinical (unspecified phase)
0.6854 Remote Similarity NPD7948 Phase 1
0.6847 Remote Similarity NPD749 Clinical (unspecified phase)
0.6845 Remote Similarity NPD2092 Phase 2
0.6845 Remote Similarity NPD2095 Phase 2
0.6845 Remote Similarity NPD2094 Phase 2
0.6844 Remote Similarity NPD7956 Approved
0.6844 Remote Similarity NPD7955 Approved
0.684 Remote Similarity NPD1466 Phase 3
0.684 Remote Similarity NPD1867 Approved
0.684 Remote Similarity NPD1467 Approved
0.6829 Remote Similarity NPD5445 Approved
0.6818 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6816 Remote Similarity NPD5903 Approved
0.6816 Remote Similarity NPD1573 Approved
0.6816 Remote Similarity NPD1575 Approved
0.6816 Remote Similarity NPD5902 Approved
0.6812 Remote Similarity NPD2096 Phase 2
0.6812 Remote Similarity NPD2091 Phase 2
0.6808 Remote Similarity NPD5512 Phase 3
0.68 Remote Similarity NPD7395 Discontinued
0.6798 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6797 Remote Similarity NPD4952 Phase 3
0.6795 Remote Similarity NPD7853 Phase 2
0.6792 Remote Similarity NPD1038 Approved
0.6792 Remote Similarity NPD802 Phase 2
0.6786 Remote Similarity NPD2433 Clinical (unspecified phase)
0.678 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6774 Remote Similarity NPD2779 Approved
0.677 Remote Similarity NPD4312 Approved
0.6766 Remote Similarity NPD5805 Approved
0.6763 Remote Similarity NPD3986 Discontinued
0.6761 Remote Similarity NPD4418 Discontinued
0.676 Remote Similarity NPD8363 Approved
0.676 Remote Similarity NPD8364 Approved
0.6758 Remote Similarity NPD3003 Approved
0.6748 Remote Similarity NPD7708 Approved
0.6742 Remote Similarity NPD4506 Discontinued
0.6741 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6741 Remote Similarity NPD4897 Phase 2
0.6741 Remote Similarity NPD3757 Clinical (unspecified phase)
0.6739 Remote Similarity NPD3263 Phase 3
0.6735 Remote Similarity NPD8091 Phase 3
0.6727 Remote Similarity NPD1392 Approved
0.6726 Remote Similarity NPD8097 Phase 3
0.6726 Remote Similarity NPD8096 Phase 3
0.6724 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6723 Remote Similarity NPD6716 Phase 1
0.6717 Remote Similarity NPD7690 Clinical (unspecified phase)
0.6717 Remote Similarity NPD1630 Approved
0.6716 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6707 Remote Similarity NPD5450 Discontinued
0.6706 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6695 Remote Similarity NPD4368 Phase 2
0.6682 Remote Similarity NPD1534 Approved
0.6681 Remote Similarity NPD7417 Discontinued
0.6681 Remote Similarity NPD2951 Discontinued
0.6681 Remote Similarity NPD5164 Discontinued
0.668 Remote Similarity NPD8463 Approved
0.6667 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6653 Remote Similarity NPD6517 Phase 3
0.6653 Remote Similarity NPD4558 Phase 2
0.6652 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6639 Remote Similarity NPD5488 Discontinued
0.6638 Remote Similarity NPD7994 Phase 2
0.6636 Remote Similarity NPD2175 Phase 3
0.6636 Remote Similarity NPD2778 Approved
0.6636 Remote Similarity NPD2177 Approved
0.6636 Remote Similarity NPD8395 Approved
0.6636 Remote Similarity NPD8396 Approved
0.6636 Remote Similarity NPD2176 Approved
0.6636 Remote Similarity NPD8098 Approved
0.6618 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6618 Remote Similarity NPD1587 Approved
0.6613 Remote Similarity NPD6228 Discontinued
0.6607 Remote Similarity NPD683 Approved
0.6605 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6602 Remote Similarity NPD8427 Approved
0.6602 Remote Similarity NPD8465 Approved
0.6602 Remote Similarity NPD8428 Approved
0.6602 Remote Similarity NPD8467 Approved
0.6602 Remote Similarity NPD8429 Approved
0.6602 Remote Similarity NPD8466 Approved
0.659 Remote Similarity NPD7946 Pre-registration
0.6587 Remote Similarity NPD6452 Discontinued
0.6585 Remote Similarity NPD750 Phase 2
0.6579 Remote Similarity NPD3354 Phase 2
0.6578 Remote Similarity NPD8349 Phase 1
0.6577 Remote Similarity NPD5429 Discontinued
0.6567 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6565 Remote Similarity NPD5506 Approved
0.6565 Remote Similarity NPD5507 Approved
0.6562 Remote Similarity NPD1592 Phase 3
0.6562 Remote Similarity NPD1166 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6558 Remote Similarity NPD1304 Clinical (unspecified phase)
0.655 Remote Similarity NPD6974 Phase 3
0.655 Remote Similarity NPD7181 Phase 3
0.6545 Remote Similarity NPD956 Clinical (unspecified phase)
0.6537 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6537 Remote Similarity NPD4049 Phase 2
0.6533 Remote Similarity NPD7470 Discontinued
0.6525 Remote Similarity NPD6263 Clinical (unspecified phase)
0.6524 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7180 Phase 3
0.652 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6516 Remote Similarity NPD2920 Discontinued
0.6515 Remote Similarity NPD1483 Discontinued
0.6513 Remote Similarity NPD3006 Discontinued
0.6511 Remote Similarity NPD5022 Discontinued
0.6511 Remote Similarity NPD5479 Discontinued
0.6511 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6507 Remote Similarity NPD4429 Discontinued
0.6502 Remote Similarity NPD6290 Phase 2
0.6502 Remote Similarity NPD7222 Phase 2
0.6502 Remote Similarity NPD7453 Approved
0.6502 Remote Similarity NPD7452 Approved
0.65 Remote Similarity NPD8460 Approved
0.65 Remote Similarity NPD4511 Phase 1
0.65 Remote Similarity NPD8425 Approved
0.65 Remote Similarity NPD8426 Approved
0.65 Remote Similarity NPD8459 Approved
0.6496 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6491 Remote Similarity NPD3389 Approved
0.6491 Remote Similarity NPD3393 Approved
0.6491 Remote Similarity NPD3394 Approved
0.6491 Remote Similarity NPD8160 Phase 2
0.6488 Remote Similarity NPD1326 Approved
0.6488 Remote Similarity NPD1325 Approved
0.6484 Remote Similarity NPD4118 Clinical (unspecified phase)
0.648 Remote Similarity NPD6530 Approved
0.648 Remote Similarity NPD6531 Approved
0.6479 Remote Similarity NPD6141 Clinical (unspecified phase)
0.6478 Remote Similarity NPD6770 Approved
0.6476 Remote Similarity NPD3945 Discontinued
0.6473 Remote Similarity NPD2510 Approved
0.6473 Remote Similarity NPD1586 Approved
0.6473 Remote Similarity NPD2509 Approved
0.6468 Remote Similarity NPD6456 Discontinued
0.6466 Remote Similarity NPD1954 Phase 1
0.646 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6457 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6456 Remote Similarity NPD5151 Clinical (unspecified phase)
0.6455 Remote Similarity NPD4601 Approved
0.6455 Remote Similarity NPD4600 Approved
0.6449 Remote Similarity NPD8102 Discontinued
0.6447 Remote Similarity NPD1638 Discovery
0.6437 Remote Similarity NPD6724 Clinical (unspecified phase)
0.6435 Remote Similarity NPD6665 Discontinued
0.6435 Remote Similarity NPD6985 Discontinued
0.6429 Remote Similarity NPD7558 Phase 2
0.6419 Remote Similarity NPD4499 Approved
0.6419 Remote Similarity NPD6803 Clinical (unspecified phase)
0.6413 Remote Similarity NPD6323 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   119405
ChEMBL   CHEMBL267855
ZINC  

Physicochemical Properties

Molecular Weight:  193.04
ALogP:  -1.5808
MLogP:  1.9
XLogP:  0.367
# Rotatable Bonds:  4
Polar Surface Area:  93.55
# H-Bond Aceptor:  3
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  14

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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