NPASS Natural Product

Natural Product: NPC274384

Natural Product ID:	NPC274384
Common Name:	Cgmp
IUPAC Name:	9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-3H-purin-6-one
Synonyms:	cyclic GMP
Molecular Formula:	C10H12N5O7P
Standard InCHIKey:	ZOOGRGPOEVQQDX-UUOKFMHZSA-N
Standard InCHI:	InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
Canonical SMILES:	O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c1[nH]c(=N)nc2O
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	cerebrospinal fluid	Geigy Scientific Tables, 8th Rev edition. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	blood	PMID[15196297]
NPO20338	Mus musculus	Species	Muridae	Eukaryota		PMID[19425150]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria		PMID[21988831]
NPO9249	Jujubae fructus	NA	NA	NA		TCMSP*
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota		TM-MC*
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota		TM-MC*

Biological Activity

Activity Type	# Activity
IC50	2
Others	6

Activity Type	# Activity
Individual Protein	7
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5439	Protein Family	Phosphodiesterase 3	Homo sapiens	IC50	=	2400	nM	8568820
NPT5222	Individual Protein	Phosphodiesterase 3B	Bos taurus	IC50	=	100	nM	8568820
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	Activity	=	16.2	%	11447229
NPT1027	Individual Protein	Multidrug resistance-associated protein 5	Homo sapiens	Activity	=	37	%	12695538
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	Activity	=	46.5	%	12036927
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	Activity	=	48	%	12695538
NPT1736	Individual Protein	ATP-binding cassette sub-family C member 11	Homo sapiens	Activity	=	73	%	15537867
NPT2773	Individual Protein	Solute carrier family 22 member 7	Homo sapiens	FC	=	97		22190696

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 NPC274384 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	458
0.1-0.2	20095
0.2-0.3	7290
0.3-0.4	2569
0.4-0.5	273
0.5-0.6	106
0.6-0.7	30
0.7-0.8	34
0.8-0.85	18
0.85-0.9	2
0.9-0.95	5
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC89147
0.9774	High Similarity	NPC251233
0.9774	High Similarity	NPC211820
0.9773	High Similarity	NPC186619
0.9701	High Similarity	NPC177169
0.963	High Similarity	NPC64705
0.963	High Similarity	NPC232408
0.9627	High Similarity	NPC318590
0.9556	High Similarity	NPC317746
0.9398	High Similarity	NPC30326
0.9394	High Similarity	NPC61198
0.9318	High Similarity	NPC262926
0.9098	High Similarity	NPC319221
0.9023	High Similarity	NPC324009
0.8851	High Similarity	NPC14590
0.8686	High Similarity	NPC320818
0.8378	Intermediate Similarity	NPC302778
0.8378	Intermediate Similarity	NPC212551
0.8367	Intermediate Similarity	NPC185991
0.8367	Intermediate Similarity	NPC85689
0.8367	Intermediate Similarity	NPC211025
0.8311	Intermediate Similarity	NPC321814
0.8267	Intermediate Similarity	NPC224076
0.8258	Intermediate Similarity	NPC327579
0.8255	Intermediate Similarity	NPC130586
0.8255	Intermediate Similarity	NPC164952
0.82	Intermediate Similarity	NPC174802
0.8194	Intermediate Similarity	NPC74306
0.8194	Intermediate Similarity	NPC315642
0.8163	Intermediate Similarity	NPC121222
0.8092	Intermediate Similarity	NPC316618
0.8092	Intermediate Similarity	NPC226245
0.8054	Intermediate Similarity	NPC326694
0.8	Intermediate Similarity	NPC161224
0.7962	Intermediate Similarity	NPC261595
0.7959	Intermediate Similarity	NPC156461
0.7959	Intermediate Similarity	NPC21448
0.7959	Intermediate Similarity	NPC107374
0.7911	Intermediate Similarity	NPC321458
0.7911	Intermediate Similarity	NPC324033
0.7905	Intermediate Similarity	NPC189068
0.7905	Intermediate Similarity	NPC164665
0.7852	Intermediate Similarity	NPC309832
0.7852	Intermediate Similarity	NPC219313
0.7852	Intermediate Similarity	NPC269827
0.7834	Intermediate Similarity	NPC323091
0.7823	Intermediate Similarity	NPC229974
0.7712	Intermediate Similarity	NPC321052
0.7687	Intermediate Similarity	NPC209525
0.7687	Intermediate Similarity	NPC161659
0.7628	Intermediate Similarity	NPC54320
0.7628	Intermediate Similarity	NPC311197
0.7628	Intermediate Similarity	NPC313754
0.7597	Intermediate Similarity	NPC472816
0.7584	Intermediate Similarity	NPC314152
0.7568	Intermediate Similarity	NPC317821
0.7564	Intermediate Similarity	NPC52238
0.7561	Intermediate Similarity	NPC326529
0.7516	Intermediate Similarity	NPC239737
0.7515	Intermediate Similarity	NPC319100
0.7515	Intermediate Similarity	NPC189261
0.7515	Intermediate Similarity	NPC324198
0.7468	Intermediate Similarity	NPC150853
0.7423	Intermediate Similarity	NPC326082
0.7372	Intermediate Similarity	NPC207633
0.7267	Intermediate Similarity	NPC129756
0.7179	Intermediate Similarity	NPC136349
0.7044	Intermediate Similarity	NPC328479
0.6974	Remote Similarity	NPC33996
0.6933	Remote Similarity	NPC195140
0.6857	Remote Similarity	NPC313547
0.6768	Remote Similarity	NPC93365
0.6744	Remote Similarity	NPC313897
0.6726	Remote Similarity	NPC324484
0.6706	Remote Similarity	NPC290959
0.6691	Remote Similarity	NPC59314
0.6686	Remote Similarity	NPC325906
0.6594	Remote Similarity	NPC119133
0.6573	Remote Similarity	NPC63433
0.6556	Remote Similarity	NPC313514
0.6549	Remote Similarity	NPC41958
0.6471	Remote Similarity	NPC293163
0.6389	Remote Similarity	NPC24589
0.6379	Remote Similarity	NPC222174
0.6374	Remote Similarity	NPC282458
0.6374	Remote Similarity	NPC78941
0.6331	Remote Similarity	NPC10466
0.6257	Remote Similarity	NPC321393
0.6207	Remote Similarity	NPC33382
0.6204	Remote Similarity	NPC320256
0.6171	Remote Similarity	NPC125659
0.6171	Remote Similarity	NPC168702
0.6165	Remote Similarity	NPC107160
0.6154	Remote Similarity	NPC21461
0.6149	Remote Similarity	NPC240084
0.6082	Remote Similarity	NPC157821
0.6062	Remote Similarity	NPC276373
0.6031	Remote Similarity	NPC5802
0.5991	Remote Similarity	NPC158055
0.598	Remote Similarity	NPC250178
0.5897	Remote Similarity	NPC180462
0.5827	Remote Similarity	NPC90240
0.5813	Remote Similarity	NPC57279
0.5808	Remote Similarity	NPC174020
0.5806	Remote Similarity	NPC109322
0.5796	Remote Similarity	NPC144223
0.5758	Remote Similarity	NPC103388
0.5694	Remote Similarity	NPC476561
0.569	Remote Similarity	NPC60537
0.5687	Remote Similarity	NPC287876
0.5671	Remote Similarity	NPC470141
0.5669	Remote Similarity	NPC248007
0.5643	Remote Similarity	NPC280946
0.5643	Remote Similarity	NPC226769
0.5643	Remote Similarity	NPC6166
0.5625	Remote Similarity	NPC14330
0.5603	Remote Similarity	NPC120887
0.5602	Remote Similarity	NPC210947

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC274384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	2070
0.2-0.3	3788
0.3-0.4	2225
0.4-0.5	671
0.5-0.6	157
0.6-0.7	54
0.7-0.8	50
0.8-0.85	11
0.85-0.9	1
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9394	High Similarity	NPD252	Clinical (unspecified phase)
0.9286	High Similarity	NPD3086	Phase 3
0.9214	High Similarity	NPD3085	Phase 1
0.9034	High Similarity	NPD4074	Clinical (unspecified phase)
0.903	High Similarity	NPD194	Clinical (unspecified phase)
0.9015	High Similarity	NPD9632	Phase 3
0.8978	High Similarity	NPD549	Approved
0.8367	Intermediate Similarity	NPD283	Approved
0.8267	Intermediate Similarity	NPD169	Phase 2
0.8258	Intermediate Similarity	NPD9607	Approved
0.8255	Intermediate Similarity	NPD338	Approved
0.8255	Intermediate Similarity	NPD242	Approved
0.82	Intermediate Similarity	NPD339	Approved
0.8194	Intermediate Similarity	NPD582	Approved
0.8182	Intermediate Similarity	NPD9606	Approved
0.806	Intermediate Similarity	NPD9409	Discontinued
0.8014	Intermediate Similarity	NPD209	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD353	Discontinued
0.7962	Intermediate Similarity	NPD247	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD250	Approved
0.7959	Intermediate Similarity	NPD249	Approved
0.7955	Intermediate Similarity	NPD9374	Approved
0.7943	Intermediate Similarity	NPD545	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD307	Approved
0.7852	Intermediate Similarity	NPD186	Discovery
0.7852	Intermediate Similarity	NPD195	Approved
0.7829	Intermediate Similarity	NPD536	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD547	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4716	Approved
0.7803	Intermediate Similarity	NPD9373	Approved
0.7758	Intermediate Similarity	NPD4744	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1369	Phase 2
0.7662	Intermediate Similarity	NPD1750	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD218	Approved
0.7628	Intermediate Similarity	NPD220	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD219	Phase 3
0.7628	Intermediate Similarity	NPD217	Approved
0.7628	Intermediate Similarity	NPD216	Approved
0.7628	Intermediate Similarity	NPD2624	Phase 2
0.7628	Intermediate Similarity	NPD2646	Discontinued
0.7584	Intermediate Similarity	NPD185	Approved
0.7548	Intermediate Similarity	NPD3107	Discontinued
0.7517	Intermediate Similarity	NPD1430	Approved
0.7517	Intermediate Similarity	NPD1431	Approved
0.7516	Intermediate Similarity	NPD1732	Phase 3
0.7515	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD166	Approved
0.7451	Intermediate Similarity	NPD775	Approved
0.745	Intermediate Similarity	NPD193	Suspended
0.7436	Intermediate Similarity	NPD214	Approved
0.7436	Intermediate Similarity	NPD213	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7988	Suspended
0.7365	Intermediate Similarity	NPD1412	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9375	Discontinued
0.7329	Intermediate Similarity	NPD3083	Approved
0.7315	Intermediate Similarity	NPD1808	Phase 1
0.7181	Intermediate Similarity	NPD1120	Approved
0.7181	Intermediate Similarity	NPD1121	Approved
0.7179	Intermediate Similarity	NPD548	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2647	Phase 3
0.7103	Intermediate Similarity	NPD515	Phase 1
0.7086	Intermediate Similarity	NPD2632	Approved
0.7086	Intermediate Similarity	NPD2630	Approved
0.7086	Intermediate Similarity	NPD2631	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4054	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD9605	Phase 3
0.7041	Intermediate Similarity	NPD5666	Phase 2
0.6929	Remote Similarity	NPD9584	Phase 2
0.6901	Remote Similarity	NPD9360	Approved
0.6875	Remote Similarity	NPD7842	Phase 2
0.6857	Remote Similarity	NPD1692	Approved
0.6783	Remote Similarity	NPD237	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD248	Discontinued
0.6709	Remote Similarity	NPD7158	Phase 1
0.6691	Remote Similarity	NPD8837	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1776	Approved
0.6686	Remote Similarity	NPD1777	Approved
0.6685	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5682	Phase 3
0.6685	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9633	Phase 3
0.6667	Remote Similarity	NPD798	Discontinued
0.665	Remote Similarity	NPD6381	Phase 2
0.6647	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.66	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD9291	Approved
0.6577	Remote Similarity	NPD9408	Phase 3
0.6556	Remote Similarity	NPD7138	Phase 2
0.6547	Remote Similarity	NPD1816	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6036	Suspended
0.6409	Remote Similarity	NPD1063	Phase 2
0.6383	Remote Similarity	NPD9417	Phase 3
0.6383	Remote Similarity	NPD9416	Phase 3
0.6259	Remote Similarity	NPD1368	Approved
0.6258	Remote Similarity	NPD282	Approved
0.625	Remote Similarity	NPD3696	Approved
0.625	Remote Similarity	NPD3695	Approved
0.6242	Remote Similarity	NPD1119	Phase 2
0.6205	Remote Similarity	NPD3708	Phase 2
0.6186	Remote Similarity	NPD2876	Phase 3
0.6186	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD2824	Phase 2
0.6121	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5080	Phase 2
0.6111	Remote Similarity	NPD2253	Discontinued
0.6098	Remote Similarity	NPD171	Discontinued
0.6077	Remote Similarity	NPD1046	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD5340	Clinical (unspecified phase)
0.607	Remote Similarity	NPD5079	Phase 2
0.6065	Remote Similarity	NPD1356	Approved
0.6065	Remote Similarity	NPD1354	Approved
0.6065	Remote Similarity	NPD1355	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD9650	Phase 3
0.6042	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD4812	Phase 1
0.6036	Remote Similarity	NPD231	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD9406	Approved
0.5991	Remote Similarity	NPD6840	Approved
0.5963	Remote Similarity	NPD7486	Phase 1
0.5962	Remote Similarity	NPD1127	Approved
0.5962	Remote Similarity	NPD1128	Approved
0.5951	Remote Similarity	NPD1118	Discontinued
0.5943	Remote Similarity	NPD5768	Phase 2
0.5939	Remote Similarity	NPD4240	Approved
0.5935	Remote Similarity	NPD281	Approved
0.5879	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD2902	Phase 2
0.5821	Remote Similarity	NPD4495	Phase 1
0.5805	Remote Similarity	NPD2604	Approved
0.5805	Remote Similarity	NPD3697	Discontinued
0.5802	Remote Similarity	NPD535	Approved
0.5782	Remote Similarity	NPD284	Phase 1
0.5774	Remote Similarity	NPD1730	Discontinued
0.5765	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD3139	Phase 3
0.5723	Remote Similarity	NPD1731	Clinical (unspecified phase)
0.5695	Remote Similarity	NPD3138	Phase 3
0.569	Remote Similarity	NPD2180	Approved
0.5687	Remote Similarity	NPD8829	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD9084	Phase 2
0.5642	Remote Similarity	NPD527	Clinical (unspecified phase)

Structure

CID274384 OpenBabel06191716082D 23 26 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8587 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8097 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8587 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5529 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3939 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1860 -3.9344 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8097 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6508 -2.2872 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3450 -2.6473 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5039 -1.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 12 2 0 0 0 0 2 15 1 0 0 0 0 3 1 1 6 0 0 0 3 6 1 0 0 0 0 3 21 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 5 16 1 1 0 0 0 6 22 1 1 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 15 1 6 0 0 0 9 21 1 0 0 0 0 10 11 2 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 18 23 1 0 0 0 0 19 23 2 0 0 0 0 20 23 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	24316
ChEMBL	CHEMBL395336
ZINC

Physicochemical Properties

Molecular Weight:	345.05
ALogP:	-1.542
MLogP:	1.13
XLogP:	-2.712
# Rotatable Bonds:	4
Polar Surface Area:	181.32
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	23

Download Data

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General Info & Identifiers & Properties
Structure MOL file
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Biological Activities
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