Natural Product: NPC53011

Natural Product ID:  NPC53011
Common Name:   Phaeocaulisin B
IUPAC Name:   (3aR,5R,5aS,8R,8aR)-5,8-dihydroxy-1,5,8-trimethyl-4,5a,6,7,8a,9-hexahydro-3aH-azuleno[6,5-b]furan-2-one
Synonyms:  
Molecular Formula:   C15H22O4
Standard InCHIKey:  BQDXDGDOYPUUOD-PGKPSXLWSA-N
Standard InCHI:  InChI=1S/C15H22O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h10-12,17-18H,4-7H2,1-3H3/t10-,11+,12+,14+,15+/m0/s1
Canonical SMILES:  O=C1O[C@H]2C(=C1C)C[C@@H]1[C@@H]([C@](C2)(C)O)CC[C@@]1(C)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
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota Rhizomes PMID[23755850]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1900 nM 19761234

  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 NPC53011 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 NPC154893
1.0 High Similarity NPC37005
1.0 High Similarity NPC16887
0.9259 High Similarity NPC290052
0.8764 High Similarity NPC98165
0.8652 High Similarity NPC37408
0.8488 Intermediate Similarity NPC191283
0.8471 Intermediate Similarity NPC287015
0.8471 Intermediate Similarity NPC146850
0.8444 Intermediate Similarity NPC220221
0.8444 Intermediate Similarity NPC469873
0.8276 Intermediate Similarity NPC45957
0.8276 Intermediate Similarity NPC471657
0.8261 Intermediate Similarity NPC477949
0.8256 Intermediate Similarity NPC245434
0.8242 Intermediate Similarity NPC52044
0.8242 Intermediate Similarity NPC67584
0.8222 Intermediate Similarity NPC272293
0.8222 Intermediate Similarity NPC40821
0.8222 Intermediate Similarity NPC32862
0.8202 Intermediate Similarity NPC471184
0.8182 Intermediate Similarity NPC79549
0.8152 Intermediate Similarity NPC213078
0.8132 Intermediate Similarity NPC477131
0.8132 Intermediate Similarity NPC127019
0.8132 Intermediate Similarity NPC470013
0.8132 Intermediate Similarity NPC470010
0.8132 Intermediate Similarity NPC323008
0.8132 Intermediate Similarity NPC262133
0.809 Intermediate Similarity NPC32922
0.809 Intermediate Similarity NPC212664
0.809 Intermediate Similarity NPC215556
0.8065 Intermediate Similarity NPC161493
0.8046 Intermediate Similarity NPC471185
0.8043 Intermediate Similarity NPC170120
0.8043 Intermediate Similarity NPC213698
0.8043 Intermediate Similarity NPC329435
0.8 Intermediate Similarity NPC301969
0.8 Intermediate Similarity NPC37607
0.8 Intermediate Similarity NPC216284
0.7979 Intermediate Similarity NPC221615
0.7935 Intermediate Similarity NPC198853
0.7912 Intermediate Similarity NPC155215
0.7912 Intermediate Similarity NPC131209
0.7912 Intermediate Similarity NPC133698
0.7912 Intermediate Similarity NPC475925
0.7841 Intermediate Similarity NPC284534
0.7841 Intermediate Similarity NPC204105
0.7841 Intermediate Similarity NPC300082
0.7826 Intermediate Similarity NPC258216
0.7826 Intermediate Similarity NPC135776
0.7812 Intermediate Similarity NPC477950
0.7812 Intermediate Similarity NPC150923
0.7778 Intermediate Similarity NPC91248
0.7766 Intermediate Similarity NPC24956
0.7766 Intermediate Similarity NPC18019
0.7753 Intermediate Similarity NPC67493
0.7742 Intermediate Similarity NPC281775
0.7742 Intermediate Similarity NPC96541
0.7692 Intermediate Similarity NPC155935
0.766 Intermediate Similarity NPC472873
0.766 Intermediate Similarity NPC304886
0.766 Intermediate Similarity NPC163228
0.7647 Intermediate Similarity NPC23187
0.7614 Intermediate Similarity NPC111409
0.7614 Intermediate Similarity NPC245665
0.7609 Intermediate Similarity NPC297474
0.7609 Intermediate Similarity NPC54065
0.7609 Intermediate Similarity NPC35809
0.7586 Intermediate Similarity NPC59994
0.7586 Intermediate Similarity NPC78677
0.7582 Intermediate Similarity NPC217983
0.7582 Intermediate Similarity NPC207114
0.7582 Intermediate Similarity NPC178875
0.7582 Intermediate Similarity NPC224652
0.7558 Intermediate Similarity NPC226226
0.7558 Intermediate Similarity NPC55304
0.7556 Intermediate Similarity NPC187661
0.7556 Intermediate Similarity NPC64153
0.7556 Intermediate Similarity NPC137253
0.7551 Intermediate Similarity NPC86077
0.7529 Intermediate Similarity NPC476439
0.7528 Intermediate Similarity NPC32223
0.7528 Intermediate Similarity NPC156485
0.7527 Intermediate Similarity NPC171360
0.7527 Intermediate Similarity NPC184063
0.7527 Intermediate Similarity NPC249034
0.7527 Intermediate Similarity NPC63193
0.7527 Intermediate Similarity NPC57304
0.7527 Intermediate Similarity NPC293001
0.7527 Intermediate Similarity NPC133888
0.7527 Intermediate Similarity NPC29821
0.7527 Intermediate Similarity NPC35959
0.7526 Intermediate Similarity NPC70865
0.75 Intermediate Similarity NPC4986
0.75 Intermediate Similarity NPC213947
0.75 Intermediate Similarity NPC472872
0.75 Intermediate Similarity NPC220217
0.75 Intermediate Similarity NPC108475
0.75 Intermediate Similarity NPC243998
0.75 Intermediate Similarity NPC223450
0.75 Intermediate Similarity NPC170143
0.75 Intermediate Similarity NPC54737
0.75 Intermediate Similarity NPC119855
0.7475 Intermediate Similarity NPC10232
0.7475 Intermediate Similarity NPC196471
0.7475 Intermediate Similarity NPC97487
0.7475 Intermediate Similarity NPC472821
0.7475 Intermediate Similarity NPC189588
0.7475 Intermediate Similarity NPC160583
0.7475 Intermediate Similarity NPC124881
0.7475 Intermediate Similarity NPC187302
0.7474 Intermediate Similarity NPC476053
0.7473 Intermediate Similarity NPC471796
0.7473 Intermediate Similarity NPC118601
0.7471 Intermediate Similarity NPC156658
0.7471 Intermediate Similarity NPC258965
0.7449 Intermediate Similarity NPC171759
0.7449 Intermediate Similarity NPC25177
0.7449 Intermediate Similarity NPC222875
0.7449 Intermediate Similarity NPC247701
0.7449 Intermediate Similarity NPC268829
0.7449 Intermediate Similarity NPC475099
0.7449 Intermediate Similarity NPC295110
0.7447 Intermediate Similarity NPC110022
0.7447 Intermediate Similarity NPC471483
0.7444 Intermediate Similarity NPC235792
0.7426 Intermediate Similarity NPC26617
0.7423 Intermediate Similarity NPC45125
0.7419 Intermediate Similarity NPC209816
0.7419 Intermediate Similarity NPC473448
0.7419 Intermediate Similarity NPC19087
0.7416 Intermediate Similarity NPC471340
0.7416 Intermediate Similarity NPC128246
0.7416 Intermediate Similarity NPC321385
0.7412 Intermediate Similarity NPC476317
0.7396 Intermediate Similarity NPC113433
0.7396 Intermediate Similarity NPC319861
0.7396 Intermediate Similarity NPC320231
0.7379 Intermediate Similarity NPC15551
0.7374 Intermediate Similarity NPC470972
0.7368 Intermediate Similarity NPC472467
0.7368 Intermediate Similarity NPC90453
0.7363 Intermediate Similarity NPC56593
0.7363 Intermediate Similarity NPC477668
0.7347 Intermediate Similarity NPC280963
0.7347 Intermediate Similarity NPC471381
0.7347 Intermediate Similarity NPC130792
0.7347 Intermediate Similarity NPC186861
0.734 Intermediate Similarity NPC78594
0.734 Intermediate Similarity NPC290651
0.734 Intermediate Similarity NPC158061
0.734 Intermediate Similarity NPC221282
0.7333 Intermediate Similarity NPC224386
0.7333 Intermediate Similarity NPC194859
0.7327 Intermediate Similarity NPC166115
0.7327 Intermediate Similarity NPC470980
0.732 Intermediate Similarity NPC181151
0.732 Intermediate Similarity NPC471150
0.732 Intermediate Similarity NPC311904
0.7312 Intermediate Similarity NPC38392
0.7308 Intermediate Similarity NPC71680
0.7303 Intermediate Similarity NPC246076
0.7294 Intermediate Similarity NPC329852
0.7292 Intermediate Similarity NPC224689
0.7292 Intermediate Similarity NPC471915
0.7292 Intermediate Similarity NPC111273
0.7283 Intermediate Similarity NPC270270
0.7283 Intermediate Similarity NPC24728
0.7283 Intermediate Similarity NPC160138
0.7282 Intermediate Similarity NPC59489
0.7282 Intermediate Similarity NPC139838
0.7273 Intermediate Similarity NPC80622
0.7263 Intermediate Similarity NPC473273
0.7263 Intermediate Similarity NPC308656
0.7263 Intermediate Similarity NPC153590
0.7263 Intermediate Similarity NPC473234
0.7263 Intermediate Similarity NPC60386
0.7263 Intermediate Similarity NPC473263
0.7263 Intermediate Similarity NPC472641
0.7263 Intermediate Similarity NPC472640
0.7238 Intermediate Similarity NPC241477
0.7234 Intermediate Similarity NPC472642
0.7234 Intermediate Similarity NPC312042
0.7228 Intermediate Similarity NPC472822
0.7228 Intermediate Similarity NPC200861
0.7222 Intermediate Similarity NPC231601
0.7222 Intermediate Similarity NPC472473
0.7216 Intermediate Similarity NPC126156
0.7216 Intermediate Similarity NPC475304
0.7216 Intermediate Similarity NPC91771
0.7216 Intermediate Similarity NPC142529
0.7212 Intermediate Similarity NPC48305
0.7212 Intermediate Similarity NPC474923
0.7209 Intermediate Similarity NPC469880
0.7204 Intermediate Similarity NPC471149
0.7191 Intermediate Similarity NPC471661
0.7191 Intermediate Similarity NPC126248
0.7188 Intermediate Similarity NPC474338
0.7174 Intermediate Similarity NPC261253

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC53011 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
0.75 Intermediate Similarity NPD1695 Approved
0.7444 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD6053 Discontinued
0.7174 Intermediate Similarity NPD4249 Approved
0.7097 Intermediate Similarity NPD4250 Approved
0.7097 Intermediate Similarity NPD4251 Approved
0.7048 Intermediate Similarity NPD6371 Approved
0.69 Remote Similarity NPD7638 Approved
0.6889 Remote Similarity NPD4819 Approved
0.6889 Remote Similarity NPD4822 Approved
0.6889 Remote Similarity NPD4821 Approved
0.6889 Remote Similarity NPD4820 Approved
0.6889 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7838 Discovery
0.6848 Remote Similarity NPD5362 Discontinued
0.6832 Remote Similarity NPD7640 Approved
0.6832 Remote Similarity NPD7639 Approved
0.6768 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6757 Remote Similarity NPD7327 Approved
0.6757 Remote Similarity NPD7328 Approved
0.6701 Remote Similarity NPD6698 Approved
0.6701 Remote Similarity NPD46 Approved
0.6699 Remote Similarity NPD7632 Discontinued
0.6696 Remote Similarity NPD7516 Approved
0.6667 Remote Similarity NPD5331 Approved
0.6667 Remote Similarity NPD4271 Approved
0.6667 Remote Similarity NPD5332 Approved
0.6667 Remote Similarity NPD4268 Approved
0.6637 Remote Similarity NPD8377 Approved
0.6637 Remote Similarity NPD8294 Approved
0.663 Remote Similarity NPD4790 Discontinued
0.6579 Remote Similarity NPD8033 Approved
0.6579 Remote Similarity NPD8380 Approved
0.6579 Remote Similarity NPD8335 Approved
0.6579 Remote Similarity NPD8379 Approved
0.6579 Remote Similarity NPD8378 Approved
0.6579 Remote Similarity NPD8296 Approved
0.6559 Remote Similarity NPD6435 Approved
0.6531 Remote Similarity NPD5785 Approved
0.6496 Remote Similarity NPD7507 Approved
0.6481 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6442 Remote Similarity NPD5344 Discontinued
0.6436 Remote Similarity NPD5695 Phase 3
0.6429 Remote Similarity NPD6051 Approved
0.6429 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6422 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6389 Remote Similarity NPD6686 Approved
0.6354 Remote Similarity NPD5363 Approved
0.6346 Remote Similarity NPD6648 Approved
0.6344 Remote Similarity NPD5368 Approved
0.6333 Remote Similarity NPD7319 Approved
0.6316 Remote Similarity NPD7154 Phase 3
0.6311 Remote Similarity NPD6084 Phase 2
0.6311 Remote Similarity NPD6083 Phase 2
0.63 Remote Similarity NPD7637 Suspended
0.6293 Remote Similarity NPD7503 Approved
0.6277 Remote Similarity NPD5369 Approved
0.625 Remote Similarity NPD5696 Approved
0.625 Remote Similarity NPD8029 Clinical (unspecified phase)
0.625 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6239 Remote Similarity NPD7320 Approved
0.6211 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6211 Remote Similarity NPD4269 Approved
0.6211 Remote Similarity NPD4270 Approved
0.6204 Remote Similarity NPD6008 Approved
0.6204 Remote Similarity NPD7128 Approved
0.6204 Remote Similarity NPD6402 Approved
0.6204 Remote Similarity NPD6675 Approved
0.6204 Remote Similarity NPD5739 Approved
0.6186 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6176 Remote Similarity NPD5282 Discontinued
0.6147 Remote Similarity NPD5701 Approved
0.6147 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6147 Remote Similarity NPD5697 Approved
0.6146 Remote Similarity NPD6695 Phase 3
0.6139 Remote Similarity NPD5693 Phase 1
0.6129 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6122 Remote Similarity NPD5786 Approved
0.6095 Remote Similarity NPD4225 Approved
0.6091 Remote Similarity NPD6881 Approved
0.6091 Remote Similarity NPD6899 Approved
0.6082 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6042 Remote Similarity NPD5209 Approved
0.6036 Remote Similarity NPD6012 Approved
0.6036 Remote Similarity NPD6014 Approved
0.6036 Remote Similarity NPD6372 Approved
0.6036 Remote Similarity NPD6013 Approved
0.6036 Remote Similarity NPD6373 Approved
0.602 Remote Similarity NPD1694 Approved
0.6 Remote Similarity NPD6412 Phase 2
0.6 Remote Similarity NPD4252 Approved
0.6 Remote Similarity NPD6903 Approved
0.5982 Remote Similarity NPD7290 Approved
0.5982 Remote Similarity NPD6883 Approved
0.5982 Remote Similarity NPD7102 Approved
0.598 Remote Similarity NPD5284 Approved
0.598 Remote Similarity NPD7983 Approved
0.598 Remote Similarity NPD5281 Approved
0.5965 Remote Similarity NPD4632 Approved
0.596 Remote Similarity NPD7334 Approved
0.596 Remote Similarity NPD5330 Approved
0.596 Remote Similarity NPD6409 Approved
0.596 Remote Similarity NPD7146 Approved
0.596 Remote Similarity NPD6684 Approved
0.596 Remote Similarity NPD7521 Approved
0.5946 Remote Similarity NPD6011 Approved
0.5941 Remote Similarity NPD4753 Phase 2
0.5932 Remote Similarity NPD6319 Approved
0.5929 Remote Similarity NPD6847 Approved
0.5929 Remote Similarity NPD8130 Phase 1
0.5929 Remote Similarity NPD6649 Approved
0.5929 Remote Similarity NPD6617 Approved
0.5929 Remote Similarity NPD6869 Approved
0.5929 Remote Similarity NPD6650 Approved
0.5922 Remote Similarity NPD5778 Approved
0.5922 Remote Similarity NPD6399 Phase 3
0.5922 Remote Similarity NPD5779 Approved
0.59 Remote Similarity NPD7524 Approved
0.59 Remote Similarity NPD7750 Discontinued
0.5877 Remote Similarity NPD8297 Approved
0.5877 Remote Similarity NPD6882 Approved
0.5868 Remote Similarity NPD7492 Approved
0.5856 Remote Similarity NPD6685 Approved
0.5849 Remote Similarity NPD4755 Approved
0.5842 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5833 Remote Similarity NPD6931 Approved
0.5833 Remote Similarity NPD6930 Phase 2
0.582 Remote Similarity NPD6616 Approved
0.5812 Remote Similarity NPD6009 Approved
0.5812 Remote Similarity NPD7115 Discovery
0.581 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5798 Remote Similarity NPD6059 Approved
0.5798 Remote Similarity NPD6054 Approved
0.5789 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5784 Remote Similarity NPD6080 Approved
0.5784 Remote Similarity NPD6673 Approved
0.5784 Remote Similarity NPD6904 Approved
0.578 Remote Similarity NPD5211 Phase 2
0.5772 Remote Similarity NPD8293 Discontinued
0.5772 Remote Similarity NPD7078 Approved
0.5769 Remote Similarity NPD4202 Approved
0.5758 Remote Similarity NPD3665 Phase 1
0.5758 Remote Similarity NPD3666 Approved
0.5758 Remote Similarity NPD3133 Approved
0.5755 Remote Similarity NPD4792 Clinical (unspecified phase)
0.575 Remote Similarity NPD5983 Phase 2
0.575 Remote Similarity NPD6016 Approved
0.575 Remote Similarity NPD6015 Approved
0.5743 Remote Similarity NPD4751 Clinical (unspecified phase)
0.5741 Remote Similarity NPD5286 Approved
0.5741 Remote Similarity NPD4700 Approved
0.5741 Remote Similarity NPD4696 Approved
0.5741 Remote Similarity NPD5285 Approved
0.5729 Remote Similarity NPD6929 Approved
0.5729 Remote Similarity NPD4195 Approved
0.5728 Remote Similarity NPD5692 Phase 3
0.5728 Remote Similarity NPD5207 Approved
0.5726 Remote Similarity NPD7736 Approved
0.5726 Remote Similarity NPD6274 Approved
0.5714 Remote Similarity NPD4221 Approved
0.5714 Remote Similarity NPD4223 Phase 3
0.5702 Remote Similarity NPD5988 Approved
0.5702 Remote Similarity NPD6370 Approved
0.569 Remote Similarity NPD8133 Approved
0.5686 Remote Similarity NPD5737 Approved
0.5686 Remote Similarity NPD6672 Approved
0.5686 Remote Similarity NPD5208 Approved
0.5676 Remote Similarity NPD5141 Approved
0.5673 Remote Similarity NPD7087 Discontinued
0.5673 Remote Similarity NPD6050 Approved
0.5673 Remote Similarity NPD5694 Approved
0.567 Remote Similarity NPD7514 Phase 3
0.566 Remote Similarity NPD4629 Approved
0.566 Remote Similarity NPD5210 Approved
0.5656 Remote Similarity NPD7604 Phase 2
0.5647 Remote Similarity NPD3198 Approved
0.5636 Remote Similarity NPD5226 Approved
0.5636 Remote Similarity NPD5224 Approved
0.5636 Remote Similarity NPD5225 Approved
0.5636 Remote Similarity NPD4633 Approved
0.5625 Remote Similarity NPD4211 Phase 1
0.5625 Remote Similarity NPD4238 Approved
0.5625 Remote Similarity NPD4802 Phase 2
0.56 Remote Similarity NPD4197 Approved

Structure

External Identifiers

PubChem CID   71725703
ChEMBL   CHEMBL2386501
ZINC  

Physicochemical Properties

Molecular Weight:  266.15
ALogP:  0.4415
MLogP:  2.67
XLogP:  0.881
# Rotatable Bonds:  5
Polar Surface Area:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  19

Download Data

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