NPASS Natural Product

Natural Product: NPC283751

Natural Product ID:	NPC283751
Common Name:	Deoxy Cholate
IUPAC Name:	2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
Synonyms:	Deoxy Cholate
Molecular Formula:	C26H45NO6S
Standard InCHIKey:	AWDRATDZQPNJFN-VAYUFCLWSA-N
Standard InCHI:	InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1
Canonical SMILES:	O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=NCCS(=O)(=O)O)O)C)C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota		DOI[10.1038/nbt.2488]
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	blood	PMID[14708888]
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	bile	PMID[659989]
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	Faeces	PMID[22664055]
NPO4808	Bovis calculus	NA	NA	NA		TCMSP*

Biological Activity

Activity Type	# Activity
EC50	3
IC50	1
Ki	1
Others	21

Activity Type	# Activity
Individual Protein	26

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	=	790	nM	18307294
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	Activity	=	20	%	19102680
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	Activity	=	46	%	19102680
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Activity	=	8.7	%	19102680
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Activity	=	91.5	%	19102680
NPT748	Individual Protein	Bile acid transporter	Homo sapiens	Activity	=	10	%	8132774
NPT2613	Individual Protein	Bile salt export pump	Mus musculus	Activity	=	5	%	10607905
NPT2850	Individual Protein	Multidrug resistance associated protein	Homo sapiens	Activity	=	9	%	12220224
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	IC50	=	60000	nM	12523936
NPT754	Individual Protein	Ileal bile acid transporter	Homo sapiens	Ki	=	17200	nM	9458785
NPT622	Individual Protein	Solute carrier organic anion transporter family member 2B1	Homo sapiens	Inhibition	=	85.3	%	22541068
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	61.4	%	22541068
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	81.7	%	22541068
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	12	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	117	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	65	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	57	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	18	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	119	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	FC	=	2.2		26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	104	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	17	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Activity	=	81	%	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	=	8900	nM	26435512
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	=	680	nM	26435512

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 NPC283751 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	48
0.1-0.2	1554
0.2-0.3	15040
0.3-0.4	7436
0.4-0.5	4563
0.5-0.6	1907
0.6-0.7	319
0.7-0.8	15
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC320478
0.9762	High Similarity	NPC247891
0.9762	High Similarity	NPC159390
0.9762	High Similarity	NPC133995
0.9524	High Similarity	NPC317363
0.8367	Intermediate Similarity	NPC478053
0.8202	Intermediate Similarity	NPC323958
0.7978	Intermediate Similarity	NPC175419
0.7865	Intermediate Similarity	NPC323180
0.7802	Intermediate Similarity	NPC321340
0.7802	Intermediate Similarity	NPC171698
0.7802	Intermediate Similarity	NPC119633
0.7802	Intermediate Similarity	NPC270957
0.764	Intermediate Similarity	NPC192456
0.7412	Intermediate Similarity	NPC478103
0.7241	Intermediate Similarity	NPC478130
0.7079	Intermediate Similarity	NPC477601
0.7079	Intermediate Similarity	NPC477602
0.7079	Intermediate Similarity	NPC473916
0.7073	Intermediate Similarity	NPC114891
0.7065	Intermediate Similarity	NPC109533
0.7024	Intermediate Similarity	NPC142712
0.6977	Remote Similarity	NPC107919
0.6977	Remote Similarity	NPC66407
0.6951	Remote Similarity	NPC148174
0.6951	Remote Similarity	NPC218585
0.6951	Remote Similarity	NPC71460
0.6949	Remote Similarity	NPC473549
0.6941	Remote Similarity	NPC473230
0.6941	Remote Similarity	NPC48079
0.6941	Remote Similarity	NPC475884
0.6915	Remote Similarity	NPC246956
0.6905	Remote Similarity	NPC474380
0.6905	Remote Similarity	NPC473276
0.6905	Remote Similarity	NPC41577
0.6905	Remote Similarity	NPC477603
0.6897	Remote Similarity	NPC192192
0.6897	Remote Similarity	NPC251201
0.6897	Remote Similarity	NPC232925
0.6897	Remote Similarity	NPC63588
0.6863	Remote Similarity	NPC473537
0.686	Remote Similarity	NPC472741
0.6824	Remote Similarity	NPC44122
0.6818	Remote Similarity	NPC109457
0.6818	Remote Similarity	NPC187471
0.6818	Remote Similarity	NPC100586
0.6818	Remote Similarity	NPC1340
0.6818	Remote Similarity	NPC470071
0.6818	Remote Similarity	NPC157422
0.6818	Remote Similarity	NPC127094
0.6818	Remote Similarity	NPC252182
0.6796	Remote Similarity	NPC475249
0.6796	Remote Similarity	NPC252564
0.6786	Remote Similarity	NPC118937
0.6786	Remote Similarity	NPC167995
0.6786	Remote Similarity	NPC69149
0.6786	Remote Similarity	NPC281540
0.6786	Remote Similarity	NPC159654
0.6782	Remote Similarity	NPC299948
0.6782	Remote Similarity	NPC254037
0.6782	Remote Similarity	NPC470830
0.6782	Remote Similarity	NPC129829
0.6782	Remote Similarity	NPC241085
0.6782	Remote Similarity	NPC477820
0.6744	Remote Similarity	NPC475172
0.6742	Remote Similarity	NPC470610
0.6742	Remote Similarity	NPC153719
0.6739	Remote Similarity	NPC329117
0.6731	Remote Similarity	NPC201712
0.6705	Remote Similarity	NPC282454
0.6705	Remote Similarity	NPC231945
0.6667	Remote Similarity	NPC475518
0.6667	Remote Similarity	NPC48795
0.6667	Remote Similarity	NPC304499
0.6632	Remote Similarity	NPC477599
0.6629	Remote Similarity	NPC477823
0.6629	Remote Similarity	NPC473279
0.6629	Remote Similarity	NPC157777
0.6629	Remote Similarity	NPC477822
0.6629	Remote Similarity	NPC195530
0.6629	Remote Similarity	NPC324984
0.6629	Remote Similarity	NPC473552
0.6629	Remote Similarity	NPC131506
0.6629	Remote Similarity	NPC477821
0.6629	Remote Similarity	NPC323900
0.6593	Remote Similarity	NPC317242
0.6593	Remote Similarity	NPC196136
0.6593	Remote Similarity	NPC243027
0.6593	Remote Similarity	NPC158208
0.6585	Remote Similarity	NPC476735
0.6562	Remote Similarity	NPC478054
0.6556	Remote Similarity	NPC473238
0.6556	Remote Similarity	NPC232112
0.6556	Remote Similarity	NPC472341
0.6552	Remote Similarity	NPC63190
0.6522	Remote Similarity	NPC4209
0.6522	Remote Similarity	NPC163597
0.6495	Remote Similarity	NPC320824
0.6484	Remote Similarity	NPC477508
0.6484	Remote Similarity	NPC10476
0.6484	Remote Similarity	NPC192501
0.6484	Remote Similarity	NPC228994
0.6452	Remote Similarity	NPC474574
0.6452	Remote Similarity	NPC477227
0.6452	Remote Similarity	NPC192046
0.6452	Remote Similarity	NPC302578
0.6452	Remote Similarity	NPC185915
0.6452	Remote Similarity	NPC11907
0.6452	Remote Similarity	NPC64081
0.6452	Remote Similarity	NPC105208
0.6452	Remote Similarity	NPC317913
0.6452	Remote Similarity	NPC133596
0.6452	Remote Similarity	NPC207010
0.6452	Remote Similarity	NPC128951
0.6444	Remote Similarity	NPC320549
0.6444	Remote Similarity	NPC111234
0.6444	Remote Similarity	NPC156277
0.6444	Remote Similarity	NPC58057
0.6444	Remote Similarity	NPC151018
0.6444	Remote Similarity	NPC126642
0.6413	Remote Similarity	NPC91387
0.6413	Remote Similarity	NPC270306
0.6413	Remote Similarity	NPC212879
0.6413	Remote Similarity	NPC70982
0.6413	Remote Similarity	NPC195155
0.6413	Remote Similarity	NPC97534
0.6413	Remote Similarity	NPC212733
0.6413	Remote Similarity	NPC174964
0.6413	Remote Similarity	NPC231256
0.6413	Remote Similarity	NPC230704
0.6413	Remote Similarity	NPC3403
0.6413	Remote Similarity	NPC231680
0.6413	Remote Similarity	NPC185536
0.6413	Remote Similarity	NPC104387
0.6413	Remote Similarity	NPC478105
0.6413	Remote Similarity	NPC240235
0.6413	Remote Similarity	NPC273366
0.6413	Remote Similarity	NPC178383
0.6408	Remote Similarity	NPC243985
0.6408	Remote Similarity	NPC280710
0.6404	Remote Similarity	NPC99264
0.6383	Remote Similarity	NPC171426
0.6383	Remote Similarity	NPC324700
0.6383	Remote Similarity	NPC34046
0.6383	Remote Similarity	NPC67657
0.6383	Remote Similarity	NPC80089
0.6383	Remote Similarity	NPC224802
0.6383	Remote Similarity	NPC147993
0.6383	Remote Similarity	NPC301707
0.6383	Remote Similarity	NPC18857
0.6381	Remote Similarity	NPC240650
0.6344	Remote Similarity	NPC472486
0.6344	Remote Similarity	NPC93662
0.6344	Remote Similarity	NPC472487
0.6344	Remote Similarity	NPC78067
0.6344	Remote Similarity	NPC91573
0.6344	Remote Similarity	NPC86305
0.6344	Remote Similarity	NPC14112
0.6344	Remote Similarity	NPC278091
0.6344	Remote Similarity	NPC470145
0.6344	Remote Similarity	NPC475742
0.6344	Remote Similarity	NPC5767
0.6333	Remote Similarity	NPC45296
0.6327	Remote Similarity	NPC478102
0.6322	Remote Similarity	NPC260116
0.6322	Remote Similarity	NPC243469
0.6322	Remote Similarity	NPC475943
0.6322	Remote Similarity	NPC190827
0.6322	Remote Similarity	NPC80463
0.6322	Remote Similarity	NPC472946
0.6316	Remote Similarity	NPC52951
0.6316	Remote Similarity	NPC477282
0.6316	Remote Similarity	NPC220379
0.6316	Remote Similarity	NPC201276
0.6316	Remote Similarity	NPC287452
0.6316	Remote Similarity	NPC81074
0.6316	Remote Similarity	NPC80891
0.6316	Remote Similarity	NPC474132
0.6316	Remote Similarity	NPC320144
0.6304	Remote Similarity	NPC192638
0.6304	Remote Similarity	NPC308440
0.6304	Remote Similarity	NPC49168
0.6304	Remote Similarity	NPC254340
0.6304	Remote Similarity	NPC5046
0.6304	Remote Similarity	NPC167702
0.6304	Remote Similarity	NPC196358
0.6304	Remote Similarity	NPC25511
0.6304	Remote Similarity	NPC280026
0.6304	Remote Similarity	NPC254509
0.6304	Remote Similarity	NPC472503
0.6304	Remote Similarity	NPC145552
0.6304	Remote Similarity	NPC62657
0.63	Remote Similarity	NPC477600
0.6292	Remote Similarity	NPC474756
0.6279	Remote Similarity	NPC292419
0.6279	Remote Similarity	NPC236099
0.6279	Remote Similarity	NPC209686
0.6279	Remote Similarity	NPC249078
0.6279	Remote Similarity	NPC290791
0.6277	Remote Similarity	NPC257191

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC283751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	63
0.1-0.2	1475
0.2-0.3	5400
0.3-0.4	1703
0.4-0.5	374
0.5-0.6	118
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9762	High Similarity	NPD6701	Clinical (unspecified phase)
0.9762	High Similarity	NPD6700	Approved
0.9419	High Similarity	NPD6703	Approved
0.9419	High Similarity	NPD6702	Approved
0.6977	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8418	Phase 2
0.6863	Remote Similarity	NPD7919	Phase 3
0.6863	Remote Similarity	NPD7920	Phase 3
0.686	Remote Similarity	NPD6705	Phase 1
0.6796	Remote Similarity	NPD8088	Phase 1
0.6739	Remote Similarity	NPD5364	Discontinued
0.6522	Remote Similarity	NPD6117	Approved
0.6517	Remote Similarity	NPD4787	Phase 1
0.6452	Remote Similarity	NPD6116	Phase 1
0.6444	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6114	Approved
0.6383	Remote Similarity	NPD6118	Approved
0.6383	Remote Similarity	NPD6697	Approved
0.6383	Remote Similarity	NPD6115	Approved
0.6304	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7525	Registered
0.6222	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD8298	Phase 2
0.6064	Remote Similarity	NPD3703	Phase 2
0.604	Remote Similarity	NPD8308	Discontinued
0.6038	Remote Similarity	NPD7991	Discontinued
0.5978	Remote Similarity	NPD4245	Approved
0.5978	Remote Similarity	NPD4789	Approved
0.5978	Remote Similarity	NPD4244	Approved
0.5934	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5360	Phase 3
0.5918	Remote Similarity	NPD6928	Phase 2
0.5877	Remote Similarity	NPD8174	Phase 2
0.587	Remote Similarity	NPD3698	Phase 2
0.5816	Remote Similarity	NPD5354	Approved
0.5784	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6942	Approved
0.5729	Remote Similarity	NPD7339	Approved
0.5714	Remote Similarity	NPD3671	Phase 1
0.5702	Remote Similarity	NPD6920	Discontinued
0.5648	Remote Similarity	NPD5771	Approved

Structure

CID283751 OpenBabel06191716092D 34 37 0 0 1 0 0 0 0 0999 V2000 -1.6923 2.9311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5613 3.4692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6435 3.7764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 4.3967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3341 5.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3614 6.0762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8697 5.5914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4442 6.3822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.9082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5267 3.2941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5544 3.3960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8461 1.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7042 4.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6099 3.6006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6923 3.9082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7320 5.0804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1016 4.0853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7865 5.2849 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2666 4.6986 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8138 5.3872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1844 4.3914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6371 3.7029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.9311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1571 4.2891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2393 4.5964 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8461 2.4426 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.0961 3.9808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0494 2.8939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8461 2.4426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9770 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9770 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 4 9 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 24 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 34 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 1 1 1 0 0 0 16 20 1 0 0 0 0 17 25 1 1 0 0 0 18 28 1 1 0 0 0 19 6 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 26 1 6 0 0 0 21 26 1 6 0 0 0 22 25 1 6 0 0 0 23 26 1 1 0 0 0 23 29 1 0 0 0 0 24 27 2 3 0 0 0 24 30 1 0 0 0 0 25 2 1 6 0 0 0 26 3 1 6 0 0 0 31 34 1 0 0 0 0 32 34 2 0 0 0 0 33 34 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	2733768
ChEMBL	CHEMBL412272
ZINC

Physicochemical Properties

Molecular Weight:	499.30
ALogP:	-0.2844
MLogP:	3.44
XLogP:	4.852
# Rotatable Bonds:	14
Polar Surface Area:	135.8
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	34

Download Data

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