ID: ALA772

Max Phase: Approved

First Approval: 1960

Molecular Formula: C33H40N2O9

Molecular Weight: 608.69

Molecule Type: Small molecule

Representations

Synonyms (6): Apoplon | Reserpine | Reserpinum | ENT-50146 | NSC-237659 | NSC-59272
Synonyms from Alternative Forms(6):

Trade Names(9): Hiserpia | Rau-sed | Reserpine | Sandril | Serpalan | Serpanray | Serpasil | Serpate | Serpivite

Canonical SMILES:  COC(=O)[C@H]1[C@H]2C[C@@H]3c4[nH]c5cc(OC)ccc5c4CCN3C[C@H]2C[C@@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)[C@@H]1OC

Standard InChI:  InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1

Standard InChI Key:  QEVHRUUCFGRFIF-MDEJGZGSSA-N

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 608.69

Molecular Weight (Monoisotopic): 608.2734

AlogP: 4.17

#Rotatable Bonds: 8

Polar Surface Area: 117.78

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 7.02

CX LogP: 3.53

CX LogD: 3.38

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.37

Np Likeness Score: 0.93

References

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86. PubChem BioAssay data set, 

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96. Unpublished dataset, 

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114. Unpublished dataset, 

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Source

Source(13):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• TP-search Transporter Database
• Withdrawn Drugs
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• RESOLUTE - Research Empowerment on Solute Carriers
• Fraunhofer HDAC6
• EU-OPENSCREEN dataset