NPASS Natural Product

Natural Product: NPC124802

Natural Product ID:	NPC124802
Common Name:	Levallorphan
IUPAC Name:
Synonyms:	Levallorphan; Lorfan; Naloxiphan
Molecular Formula:	C19H25NO
Standard InCHIKey:	OZYUPQUCAUTOBP-QXAKKESOSA-N
Standard InCHI:	InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1
Canonical SMILES:	C=CCN1CC[C@@]23[C@H]([C@H]1Cc1c3cc(cc1)O)CCCC2
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota				TM-MC*

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Biological Activity

Activity Type	# Activity
AC50	3
IC50	17
Ki	4
Others	2
Potency	14

Activity Type	# Activity
Individual Protein	6
Organism	2
Others	29
Protein Family	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1069	Individual Protein	Mu opioid receptor	Rattus norvegicus	IC50	=	0.6341	nM	21864951
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Ki	=	1.29	nM	21621410
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Ki	=	1.69	nM	21621410
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Ki	=	0.48	nM	21621410
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency		26603.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Ratio	=	3.7		6325691
NPT2	Others	Unspecified		Potency		4731.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		6007	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		26806.2	nM	PubChem BioAssay data set

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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 NPC124802 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	199
0.1-0.2	1162
0.2-0.3	3330
0.3-0.4	7755
0.4-0.5	7143
0.5-0.6	8867
0.6-0.7	2069
0.7-0.8	355
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	6

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Similarity Score	Similarity Level	Natural Product ID
0.7222	Intermediate Similarity	NPC477020
0.7222	Intermediate Similarity	NPC192135
0.7226	Intermediate Similarity	NPC180756
0.7226	Intermediate Similarity	NPC170503
0.7226	Intermediate Similarity	NPC323443

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Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC124802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	707
0.2-0.3	809
0.3-0.4	1667
0.4-0.5	2878
0.5-0.6	2031
0.6-0.7	753
0.7-0.8	112
0.8-0.85	18
0.85-0.9	4
0.9-0.95	3
0.95-1	9

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6835	Remote Similarity	NPD3026	Approved
0.6835	Remote Similarity	NPD3023	Approved
0.6839	Remote Similarity	NPD5699	Approved
0.6842	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3059	Approved

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Structure

CID124802 OpenBabel06191715482D 21 24 0 0 1 0 0 0 0 0999 V2000 -2.0029 1.3551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1200 1.1189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2500 -3.0761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0413 -2.6186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4582 -2.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9544 0.1234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7462 -0.3335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0408 -1.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7917 -0.4568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8830 0.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7915 0.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3713 -0.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9548 -1.7049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1628 -0.3338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7464 -1.2476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4577 -1.7055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1630 -1.2480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4575 -0.7913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2490 -1.2480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5381 -1.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 10 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 17 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 0 0 0 0 18 12 1 6 0 0 0 18 20 1 0 0 0 0 19 8 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	5359371
ChEMBL	CHEMBL1254682
ZINC

Physicochemical Properties

Molecular Weight:	283.19
ALogP:	-0.3827
MLogP:	3.33
XLogP:	4.303
# Rotatable Bonds:	3
Polar Surface Area:	23.47
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	21

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